Diamine derivatives, process for producing the diamine derivatives, and fungicides containing the diamine derivatives as an active ingredient

ABSTRACT

A fungicide can be provided by using, as an active ingredient, a diamine derivative of the following general formula (1): 
     
       
         
         
             
             
         
       
         
         
           
             wherein 
             R1 to R7 represent a specific substituent such as an alkyl group with 1 to 6 carbon atoms, and R8 represents an aryl group, which may be substituted or a heteroaryl group, which may be substituted.

TECHNICAL FIELD

This invention relates to novel diamine derivatives, a process forproducing the diamine derivatives, and a fungicide containing thediamine derivatives as an active ingredient.

BACKGROUND ART

Pest Control plays a significant role in cultivation of paddy rice, and,in particular, various fungicides have been developed and used againstrice blast, which is considered to be an important disease injury. Thesefungicides, however, are not always satisfactory in terms of the desiredfungicidal activity and control of the undesirable harmful effects onuseful crops. In addition, in recent years, fungi having drug-resistanthave emerged due to the frequent use of agricultural and horticulturalfungicides, and the existing fungicides do not always exhibitsatisfactory fungicidal activity. Furthermore, from the environmentalviewpoint, there have been demands for novel fungicides which are safeand capable of controlling harmful fungi at lower concentrations.

DISCLOSURE OF INVENTION

Accordingly, an object of this invention is to provide diaminederivatives, which exhibit excellent effect to control rice blast, butdoes not injure useful crops.

In order to solve the above-described problems, the present inventorssynthesized various novel diamine derivatives and various investigationsrelating to their fungicidal activities, etc., have been carried out.They have finally found the diamine derivatives, which exhibit excellenteffect to control rice blast, but not injure useful crops. As a resultthe present inventors have completed this invention.

Specifically, this invention include the following embodiments andaspects:

-   [1] A diamine derivative, represented by the following general    formula (1):

-   -   wherein    -   R1 represents an alkyl group with 1 to 6 carbon atoms provided        that the case is excluded where R1 is a tert-butyl, a cycloalkyl        group with 3 to 6 carbon atoms, an alkenyl group with 2 to 6        carbon atoms, a cycloalkenyl group with 3 to 6 carbon atoms, an        alkynyl group with 2 to 6 carbon atoms, an arylalkyl group which        may be substituted, a heteroarylalkyl group which may be        substituted, an aryl group which may be substituted, or a        heteroaryl group which may be substituted; R2 and R7        independently represent a hydrogen atom, an alkyl group with 1        to 6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms,        an alkenyl group with 2 to 6 carbon atoms, a cycloalkenyl group        with 3 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon        atoms, an arylalkyl group which may be substituted, an aryl        group which may be substituted, or an acyl group;    -   R3 and R4 independently represent a hydrogen atom, an alkyl        group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6        carbon atoms, an alkenyl group with 2 to 6 carbon atoms, a        cycloalkenyl group with 3 to 6 carbon atoms, an alkynyl group        with 2 to 6 carbon atoms, an arylalkyl group which may be        substituted, a heteroarylalkyl group which may be substituted,        an aryl group which may be substituted or a heteroaryl group        which may be substituted, or a cycloalkyl group with 3 to 6        carbon atoms including an attached carbon atom;    -   R5 and R6 independently represent a hydrogen atom, an alkyl        group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6        carbon atoms, an alkenyl group with 2 to 6 carbon atoms, a        cycloalkenyl group with 3 to 6 carbon atoms, an alkynyl group        with 2 to 6 carbon atoms, an arylalkyl group which may be        substituted, or an aryl group which may be substituted; provided        that the case is excluded where R3, R4, R5 and R6 all represent        a hydrogen atom or where any one of R3, R4, R5 and R6 represents        a methyl group which may be substituted and the others represent        a hydrogen atom, and    -   R8 represents an aryl group which may be substituted or a        heteroaryl group which may be substituted.

-   [2] The diamine derivative according to the above section [1],    wherein    -   R1 represents an alkyl group with 1 to 6 carbon atoms provided        that the case is excluded where R1 is a tert-butyl, a cycloalkyl        group with 3 to 6 carbon atoms, an alkenyl group with 2 to 6        carbon atoms, an arylalkyl group which may be substituted, a        heteroarylalkyl group which may be substituted, an aryl group        which may be substituted, or a heteroaryl group which may be        substituted;    -   R2 and R7 independently represent a hydrogen atom, an alkyl        group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6        carbon atoms, an arylalkyl group which may be substituted, an        aryl group which may be substituted, or an acyl group;    -   R3 and R4 independently represent a hydrogen atom, an alkyl        group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6        carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an        arylalkyl group which may be substituted, a heteroarylalkyl        group which may be substituted, an aryl group which may be        substituted or a heteroaryl group which may be substituted, or a        cycloalkyl group with 3 to 6 carbon atoms including an attached        carbon atom; and    -   R5 and R6 independently represent a hydrogen atom, an alkyl        group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6        carbon atoms, an arylalkyl group which may be substituted, or an        aryl group which may be substituted; provided that the case is        excluded where R3, R4, R5 and R6 all represent a hydrogen atom        or where any one of R3, R4, R5 and R6 represents a methyl group        which may be substituted and the others represent a hydrogen        atom.

-   [3] The diamine derivative according to the above section [2],    wherein    -   R2 and R7 independently represent a hydrogen atom, an alkyl        group with 1 to 6 carbon atoms, or an acyl group;    -   R3 and R4 independently represent a hydrogen atom, an alkyl        group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6        carbon atoms, an arylalkyl group which maybe substituted, an        aryl group which may be substituted, or a cycloalkyl group with        3 to 6 carbon atoms including an attached carbon atom; and    -   R5 and R6 independently represent a hydrogen atom, an alkyl        group with 1 to 6 carbon atoms, an arylalkyl group which may be        substituted, or an aryl group which may be substituted; provided        that the case is excluded where R3, R4, R5 and R6 all represent        a hydrogen atom or where any one of R3, R4, R5 and R6 represents        a methyl group which may be substituted and the others represent        a hydrogen atom.

-   [4] The diamine derivative according to the above section [3],    wherein R2 and R7 represent a hydrogen atom.

-   [5] A diamine derivative, represented by the following general    formula (9):

-   -   wherein R9 represents an alkyl group with 1 to 6 carbon atoms, a        cycloalkyl group with 3 to 6 carbon atoms, an alkenyl group with        2 to 6 carbon atoms, a cycloalkenyl group with 3 to 6 carbon        atoms, an alkynyl group with 2 to 6 carbon atoms, an arylalkyl        group which may be substituted, a heteroarylalkyl group which        may be substituted, a phenyl group, a phenyl group which is        substituted at the fourth position, or a heteroaryl group which        may be substituted;    -   R10 and R15 independently represent a hydrogen atom, an alkyl        group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6        carbon atoms, an alkenyl group with 2 to 6 carbon atoms, a        cycloalkenyl group with 3 to 6 carbon atoms, an alkynyl group        with 2 to 6 carbon atoms, an arylalkyl group which may be        substituted, an aryl group which may be substituted, or an acyl        group;    -   One of R11 and R12 represents a methyl group, and the other        represents a hydrogen atom;    -   R13 and R14 represent a hydrogen atom, respectively; and    -   R16 represents a phenyl group, a phenyl group which is        substituted at the fourth position, or a heteroaryl group which        may be substituted.

-   [6] The diamine derivative according to the above section [5],    wherein    -   R9 represents an alkyl group with 1 to 6 carbon atoms, a        cycloalkyl group with 3 to 6 carbon atoms, an alkenyl group with        2 to 6 carbon atoms, an arylalkyl group which may be        substituted, a heteroarylalkyl group which may be substituted, a        phenyl group, a phenyl group which is substituted at the fourth        position, or a heteroaryl group which may be substituted; and    -   R10 and R15 represent a hydrogen atom, an alkyl group with 1 to        6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms, an        arylalkyl group which may be substituted, an aryl group which        may be substituted, or an acyl group, independently.

-   [7] The diamine derivative according to the above section [6],    wherein R10 and R15 independently represent a hydrogen atom, an    alkyl group with 1 to 6 carbon atoms, or an acyl group.

-   [8] The diamine derivative according to the above section [7],    wherein at R10 and R15 represent a hydrogen atom, respectively.

-   [9] A fungicide, wherein it contains the diamine derivative    according to any one of the above sections [1] to [8] as an active    ingredient.

-   [10] A process for producing the diamine derivative according to the    above section [1], wherein a compound having the following general    formula (2):

-   -   wherein    -   R1, R2, R3, R4, R5, R6 and R7 represent the same groups as those        of the compounds according to the above section [1],    -   is reacted with a compound having the following general formula        (3):

-   -   wherein    -   R8 represents the same group as that of the compound according        to the above section [1], and    -   X represents a leaving group.

-   [11] A process for producing the diamine derivative according to the    above section [1], wherein a compound of the general formula (2) is    condensed with a compound having the following general formula (4):

-   -   wherein    -   R8 represents the same group as that of the compounds according        to the above section [1].

-   [12] A process for producing the diamine derivative according to the    above section [1], wherein a compound having the following general    formula (5):

-   -   wherein    -   R2, R3, R4, R5, R6, R7 and R8 represent the same groups as those        of the compound according to the above section [1],    -   is reacted with a compound having the following general formula        (6):

-   -   wherein    -   R1 represents the same group as that of the compound according        to the above section [1], and    -   X represents a leaving group.

-   [13] A process for producing the diamine derivative according to the    above section [5], wherein a compound having the following general    formula (10):

-   -   wherein    -   R9, R10, R11, R12, R13, R14 and R15 represent the same groups as        those of the compounds according to the above section [5],    -   is reacted with a compound having the following general formula        (11):

-   -   wherein    -   R16 represents the same group as that of the compound according        to the above section [5], and    -   X represents a leaving group.

-   [14] A process for producing the diamine derivative according to the    above section [5], wherein a compound of the general formula (10) is    condensed with a compound having the following general formula (12):

-   -   wherein    -   R16 represents the same group as that of the compounds according        to the above section [5].

-   [15] A process for producing the diamine derivative according to the    above section 5, wherein a compound having the following general    formula (13):

-   -   wherein    -   R10, R11, R12, R13, R14, R15 and R16 represent the same groups        as those of the compound according to the above section [5],    -   is reacted with a compound having the following general formula        (14):

-   -   wherein    -   R9 represents the same group as that of the compound according        to the above section [5], and    -   X represents a leaving group.

BEST MODE FOR CARRYING OUT THE INVENTION

The invention will be described below more in detail.

In the diamine derivatives of the general formulas (1) and (9) and theprocess for producing the same, examples of the alkyl group with 1 to 6carbon atoms include methyl, ethyl, propyl, butyl, pentyl, hexyl, allyl,methallyl and propargyl groups; examples of the cycloalkyl group with 3to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl andcyclohexyl groups; examples of the alkenyl group with 2 to 6 carbonatoms include vinyl, propenyl, butenyl, pentenyl and hexenyl groups;examples of the cycloalkenyl group with 3 to 6 carbon atoms includecyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl groups;examples of the alkynyl group with 2 to 6 carbon atoms include ethynyl,propynyl, butynyl, pentynyl and hexynyl groups; examples of the arylgroup include phenyl and naphthyl groups; examples of the heteroarylgroup include pyridyl, pyrimidyl, thienyl, furanyl, pyrazolyl,imidazolyl, isothiazolyl, isoxazolyl, indolyl, quinolyl, benzofuranyl,benzothienyl, benzoxazolyl, benzoisoxazolyl, benzimidazolyl,benzothiazolyl and benzoisothiazolyl groups; examples of the acyl groupinclude alkylcarbonyl groups such as acetyl group and arylcarbonylgroups such as benzoyl group.

Examples of the substituent(s) of the aryl group and the heteroarylgroup include alkyl groups having 1 to 6 carbon atoms such as methyl,ethyl, propyl and butyl groups; cycloalkyl groups having 3 to 6 carbonatoms such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexylgroups; halogen-substituted alkyl groups having 1 to 4 carbon atoms suchas trifluoromethyl, difluoromethyl, bromodifluoromethyl andtrifluoroethyl groups; alkoxy groups having 1 to 4 carbon atoms such asmethoxy, ethoxy, propoxy and butoxy groups; halogen-substituted alkoxygroups having 1 to 4 carbon atoms such as trifluoromethoxy,difluoromethoxy and trifluoroethoxy groups; alkylthio groups having 1 to4 carbon atoms such as methylthio, ethylthio, propylthio and butylthiogroups; halogen-substituted alkylthio groups having 1 to 4 carbon atomssuch as trifluoromethylthio, difluoromethylthio and trifluoroethylthiogroups; alkylsulfinyl groups having 1 to 4 carbon atoms such asmethanesulfinyl, ethanesulfinyl, propanesulfinyl and butanesulfinylgroups; halogen-substituted alkylsulfinyl groups having 1 to 4 carbonatoms such as trifluoromethanesulfinyl, difluoromethanesulfinyl andtrifluoroethanesulfinyl groups; alkyl sulfonyl groups having 1 to 4carbon atoms such as methanesulfonyl, ethanesulfonyl; propanesulfonyland butanesulfonyl groups; halogen-substituted alkylsulfonyl groupshaving 1 to 4 carbon atoms such as trifluoromethanesulfonyl,difluoromethanesulfonyl and trifluoroethanesulfonyl groups,alkylsulfonamide groups having 1 to 4 carbon atoms such asmethanesulfonamide, ethanesulfonamide, propanesulfonamide andbutanesulfonamide groups; halogen-substituted alkylsulfonamide groupshaving 1 to 4 carbon atoms such as trifluoromethanesulfonamide,difluoromethanesulfonamide and trifluoroethanesulfonamide groups;halogen atoms such as fluorine, chlorine, bromine and iodine atoms; andacyl groups such as acetyl and benzoyl groups.

The aryl group and the heteroaryl group may be substituted by two ormore groups selected from them.

Examples of the methyl group, which may be substituted, include methyl,hydroxymethyl and halomethyl groups.

In the compounds of the general formulas (3), (6), (11) and (14),examples of the leaving groups include halogen atoms such as chlorineatom; alkoxy groups such as methoxy and ethoxy groups; aryloxy groupssuch as phenoxy group; and imidazole group.

The compounds of the invention represented by the general formulas (1)and (9) are novel. The compounds of formula (1) can be produced by theprocess shown by the following equation (1):

wherein

R1, R2, R3, R4, R5, R6 and R7 have the same definitions as those of thegeneral formula (2), respectively; and

R8 and X have the same definitions as those of the general formula (3),respectively.

In the equation (1), a diamine derivative of the general formula (1) canbe produced by reacting a diamine derivative of the general formula (2)or its salt with a well known carbonyl compound of the general formula(3) in a reaction containing either no solvent or a solvent(s), andeither in the absence of a base(s) or in the presence of base(s).

Examples of the base used in the reaction shown by the equation (1)include alkaline metal hydroxides such as sodium hydroxide and potassiumhydroxide; alkaline earth metal hydroxides such as magnesium hydroxideand calcium hydroxide; alkaline metal hydrides such as sodium hydrideand potassium hydride; alkaline metal alcoholates such as sodiummethoxide and sodium ethoxide; alkaline metal oxides such as sodiumoxide; carbonates such as potassium carbonate and sodium carbonate;phosphates such as tri-potassium phosphate, tri-sodium phosphate,di-potassium hydrogen phosphate, di-sodium hydrogen phosphate; acetatessuch as sodium acetate and potassium acetate; organic bases such aspyridine, 4-(dimethylamino)pyridine, triethylamine and1,8-diazabicyclo[5.4.0]undec-7-ene. At least one base can be used in theabove reaction.

The quantity of the base(s) is not particularly limited, and when atleast one of the above organic bases is used, it can also be used as asolvent.

Examples of the solvent which may be used in the reaction shown by theequation (1) include water; alcohols such as methanol, ethanol, propanoland butanol; halogenated hydrocarbons such as dichloromethane andchloroform; aromatic hydrocarbons such as benzene, toluene and xylene;aliphatic hydrocarbons such as hexane and heptane; polar aproticsolvents such as dimethylformamide (DMF), dimethylacetamide (DMA),dimethyl sulfoxide (DMSO), 1,3-dimethyl-2-imidazolidinone (DMI) and1-methyl-2-pyrrolidone (NMP); ethers such as diethyl ether, diisopropylether, 1,2-dimethoxyethane (DME), tetrahydrofuran (THF) and dioxane; andnitrites such as acetonitrile and propionitrile.

The chemical equivalent of the carbonyl compound of the general formula(3) to the compound of the general formula (2) is preferably 1 to 2, andmore preferably 1 to 1.2.

The reaction temperature and reaction time of the above reaction may bechanged over a wide range. Generally, the reaction temperature may bepreferably in the range from −20 to 200° C., more preferably from 0 to100° C., and the reaction time may be preferably in the range from 0.01to 50 hours, more preferably from 0.1 to 15 hours.

The amine derivatives and the salts thereof of the general formula (2)of the equation (1), other than commercially available ones, can beeasily produced by the method such as Gabriel's synthesis; Delepinereaction; well known amine synthesis in which cyano group, amide, imineor oxime is reduced; or synthesis described in Tetrahedron Asymmetry,vol. 11, 1907 (2000).

The compounds of the general formula (3) of the equation (1) can beproduced by conventional procedures in which a well known derivative ofcarboxylic acid of the general formula (4) is reacted with thionylchloride, oxalyl chloride, phosgene or 1,1′-carbonylbis-1H-imidazole.

The compounds of the general formula (3) of the equation (1) can also beproduced by conventional procedures in which a well known derivative ofcarboxylic acid of the general formula (4) is reacted with alcohol suchas methyl alcohol or ethyl alcohol without a catalyst or in the presenceof a catalyst.

The compounds of the invention, of the general formula (1), can also beproduced by the process shown by the following equation (2).

wherein

R1, R2, R3, R4, R5, R6 and R7 have the same definitions as in thegeneral formula (2), respectively; and

R8 has the same definition as that of the general formula (4).

In the equation (2), a diamine derivative of the general formula (1) canbe produced by condensing a diamine derivative of the general formula(2) or its salt with a well known derivative of carboxylic acid of thegeneral formula (4), in a reaction containing no solvent or asolvent(s).

Examples of the condensation agents for this case include:

-   N,N′-dicyclohexylcarbodiimide,-   1,1′-carbonylbis-1H-imidazole,-   1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride,    2-chloro-1,3-dimethylimidazorium chloride.

As the quantity of the condensation agent to the compound of the generalformula (4), the chemical equivalent of the former to the latter ispreferably 1 to 2, more preferably 1 to 1.2.

As the organic solvent(s) for this case, the same solvent(s) as thosefor the process shown by the equation (1) may be used.

Regarding the quantity of the derivative of carboxylic acid of thegeneral formula (4) to the compound of the general formula (2), thechemical equivalent of the former to the latter is preferably 1 to 2,more preferably 1 to 1.2.

The reaction temperature and reaction time of the above reaction may bechanged over a wide range. Generally, the reaction temperature may bepreferably in the range from −20 to 200° C., more preferably from 0 to100° C., and the reaction time may be preferably in the range from 0.01to 50 hours, more preferably from 0.1 to 15 hours.

The compounds of the invention of the general formula (1), can also beproduced by the process shown by the following equation (3):

wherein

R2, R3, R4, R5, R6, R7 and R8 have the same definitions as those of thegeneral formula (5), respectively; and

R1 and X have the same definitions as those of the general formula (6),respectively.

In the equation (3), a diamine derivative of the general formula (1) canbe produced by reacting a diamine derivative of the general formula (5)or its salt with a well known compound of the general formula (6) in areaction containing no solvent or a solvent(s), either in the absence ofa base(s) or in the presence of a base(s).

In this reaction, the same base(s) as those used in the equation (1) canbe used.

The quantity of the bases used is not particularly limited, and when theabove organic base(s) is used, they can also be used as a solvent.

As the solvent(s) for this case, the same solvent(s) as those used inthe process shown by the equation (1) can be used.

Regarding the quantity of the compounds of the general formula (6) tothe diamine derivatives of the general formula (5), the chemicalequivalent of the former to the latter is preferably 1 to 2, morepreferably 1 to 1.2.

The reaction temperature and reaction time of the above reaction may bechanged over a wide range. Generally, the reaction temperature may bepreferably in the range from −20 to 200° C., more preferably from 0 to100° C., and the reaction time may be preferably in the range from 0.01to 50 hours, more preferably from 0.1 to 15 hours.

The compounds of formula (9) can be produced in the same manners bysubstituting the compounds (2) to (6) in the reaction equations (1) to(3) with the compounds (10) to (14) mentioned above.

There exist asymmetric carbon atoms in the diamine derivatives of thegeneral formulas (1) and (9), depending on the type of substituent(s),and the derivatives can exist as an optical isomer, diastereoisomer,racemic modification or mixture thereof at an arbitrary rate. Theinvention embraces all isomers of these types and the mixture thereof.

The agricultural and horticultural fungicides containing the diaminederivatives of the invention represented by the general formulas (1) and(9) as an active ingredient exhibit an excellent effect to control riceblast caused by Pyricularia oryzae.

The diamine derivatives of the invention of the general formulas (1) and(9) can be used by combining them with at least one of other fungicides,agricultural chemicals such as insecticides, herbicides and plant growthregulators, soil conditioners, and fertilizer responsive substances.They can be applied in the form of a mixture preparation.

Although the diamine derivatives of the present invention may be used asthey are, they are preferably used as a formulation in the form of acomposition, which can be obtained by mixing them with a carrierincluding a solid or liquid diluent. The term “carrier” herein usedmeans a synthetic or natural, inorganic or organic materials which ismixed to help the active ingredient reach the target site and makeeasier the storage, transportation and handling of the active ingredientcompounds.

Examples of the solid carriers suitably used in the invention includeclays such as montmorillonite, kaolinite and bentonite; inorganicsubstances such as diatomaceous earth, clay, talc, vermiculite, plaster,calcium carbonate, silica gel and ammonium sulfide; vegetable organicmaterials such as soybean flour, sawdust and wheat flour; and urea.

Examples of the liquid carriers suitably used in the invention includearomatic hydrocarbons such as toluene, xylene and cumene; paraffinhydrocarbons such as kerosine and mineral oil; halogenated hydrocarbonssuch as carbon tetrachloride, chloroform and dichloroethane; ketonessuch as acetone and methyl ethyl ketone; ethers such as dioxane,tetrahydrofuran and diethylene glycol dimethyl ether; alcohols such asmethanol, ethanol, propanol and ethylene glycol; dimethylformamide;dimethyl sulfoxide; and water.

In order to enhance the effectiveness of the compounds of the invention,at least one of the following adjuvants can be used solely or in theircombination, according to the object, while taking into account theformulation of the compounds, the site of application, etc.

When aiming at emulsification, dispersion, spreading, moistening,binding and stabilization of the compounds, an adjuvant(s) may be usedfor the formulation. Examples of the adjuvants include anionicsurfactants such as ligninsulfonate, alkylbenzenesulfonate, alkylsulfateester, polyoxyalkylene alkylsulfate ester and polyoxyalkylenealkylphosphate ester; nonionic surfactants such as polyoxyalkylene alkylether, polyoxyalkylene alkylaryl ether, polyoxyalkylene alkylamine,polyoxyalkylene alkylamide, polyoxyalkylene alkyl thioether,polyoxyalkylene fatty ester, glycerol fatty ester, sorbitan fatty ester,polyoxyalkylene sorbitan fatty ester and polyoxypropylenepolyoxyethylene block copolymer; lubricants such as calcium stearate andwax; stabilizers such as isopropylhydrodiene phosphate; methylcellulose; carboxymethyl cellulose; casein; and gum arabic. Theadjuvants used are not limited to the above described ones.

The quantity of the compounds of the invention as an active ingredientis generally 0.5 to 20% by weight for dust formulation, 5 to 50% byweight for emulsifiable concentrate, 10 to 90% by weight for wettablepowder, 0.1 to 20% by weight for granular, and 10 to 90% by weight forflowable. The quantity of carrier in each formulation is generally 60 to99% by weight for dust, 40 to 95% by weight for emulsifiableconcentrate, 10 to 90% by weight for wettable powder, 80 to 99% byweight for granular, and 10 to 90% by weight for flowable, respectively.The quantity of adjuvant is generally 0.1 to 20% by weight for dust, 1to 20% by weight for emulsifiable concentrate, 0.1 to 20% by weight forwettable powder, 0.1 to 20% by weight for granular, and 0.1 to 20% byweight for flowable.

EXAMPLES

In the following, the invention will be described in further detailtaking several examples and test examples.

Example 1 Preparation ofN-(methoxycarbonyl)-N′-benzoyl-1-phenyl-1,2-ethylenediamine (CompoundNo. 66)

0.22 g of benzoyl chloride was added to 10 ml of a solution of 0.25 g ofN-(methoxycarbonyl)-1-phenylethylenediamine and 0.2 g of triethylaminein dichloromethane under ice cooling, and the mixture was stirred for 30minutes at 5° C. and at room temperature for 3 hours. The reactionmixture was rinsed with water, the organic layer was dried overmagnesium sulfate anhydrous, and the residual oily material obtainedunder a reduced pressure was purified by column chromatography on silicagel (2:1 hexane/ethyl acetate) to obtain 0.28 g of the title compound ascolorless crystals.

Example 2 Preparation ofN-(4-chlorobenzoyl)-N′-(i-propoxycarbonyl)-3-phenyl-1,2-propanediamine(Compound No. 290)

0.21 g of 1,1′-carbonylbis-1H-imidazole was added to a solution of 0.19g of 4-chlorobenzoic acid in tetrahydrofuran and stirred for 1 hour atroom temperature. Then 5 ml of a solution of 0.25 g of2-(i-propoxycarbonylamino)-3-phenylpropylamine in tetrahydrofuran wasadded to the above solution and stirred at room temperature for 4 hours.The reaction mixture was rinsed with water, the organic layer was driedover magnesium sulfate anhydrous, and the residual oily materialobtained under a reduced pressure was purified by column chromatographyon silica gel (2:1 hexane/ethyl acetate) to obtain 0.26 g of the titlecompound as colorless crystals.

Example 3 Preparation ofN-(benzyloxycarbonyl)-N′-benzoyl-1-phenyl-1,2-ethylenediamine (CompoundNo. 636)

0.12 g of triethylamine was added to 10 ml of a solution of 0.25 g ofN-benzoyl-2-phenyl-1,2-ethylenediamine hydrochloride and 0.17 g ofbenzyl chloroformate in dichloromethane under ice cooling, and themixture was stirred at 5° C. for 30 minutes and at room temperature for3 hours. The reaction mixture was rinsed with water, the organic layerwas dried over magnesium sulfate anhydrous, and the residual oilymaterial obtained under a reduced pressure was purified by columnchromatography on silica gel (2:1 hexane/ethyl acetate) to obtain 0.28 gof the title compound as colorless crystals.

Example 4 Preparation ofN-(t-butoxycarbonyl)-N′-(4-methylbenzoyl)-1-phenyl-1,2-ethylenediamine(Compound No. 504)

0.24 g of triethylamine was added to a solution of 0.22 g of di-t-butyldicarbonate and 0.25 g ofN-(4-methylbenzoyl)-2-phenyl-1,2-ethylenediamine hydrochloride indichloromethane under ice cooling, and the mixture was stirred at 5° C.for 1 hour and at room temperature for 3 hours. The reaction mixture wasrinsed with water, the organic layer was dried over magnesium sulfateanhydrous, and the residual oily material obtained under a reducedpressure was purified by column chromatography on silica gel (2:1hexane/ethyl acetate) to obtain 0.24 g of the title compound ascolorless crystals.

The compounds of the general formulas (1) and (9) which can be producedin the same manner as in Examples 1 to 4 are shown in Table 1 below. Andthe physical properties of some of the compounds are shown in Table 2.R17 to R24 in Table 1 are the substitutions shown in the followingformula (15):

In Table 1, Me represents a methyl group, Et represents an ethyl group,n-Pr represents a normal propyl group, i-Pr represents an isopropylgroup, i-Bu represents an isobutyl group, s-Bu represents a secondarybutyl group, t-Bu represents a tertiary butyl group, Ph represents aphenyl group, Bn represents a benzyl group, 1-Naph represents a1-naphtyl group, 2-Naph represents a 2-naphtyl group, c-Pr represents acyclopropyl group, c-Hex represents a cyclohexyl group, Ac represents anacetyl group, Bz represents a benzoyl group, vinyl represents an ethenylgroup, allyl represents a 2-propenyl group, propargyl represents a2-propynyl group, neopentyl represents a 2,2-dimethylpropyl group,methallyl represents a 2-methyl-2-propenyl group, and 2-thienylrepresents a thiophene-2-yl group.

TABLE 1 Comp. No. R17 R18 R19 R20 R21 R22 R23 R24 1 Me H Me H H H H Ph 2Me H Me H H H H 2-ClC6H4 3 Me H Me Me H H H 3-ClC6H4 4 Me H Me H H H H4-ClC6H4 5 Me H Me H H H H 4-MeC6H4 6 Me H Me H H H H 4-t-BuC6H4 7 Me HMe H H H H 1-Naph 8 Me H Me H H H H thiophene-2-yl 9 Me H Me H H H Hpyridine-3-yl 10 Me H Me Me H H H 4-ClC6H4 11 Me H Et H H H H Ph 12 Me HEt H H H H 2-ClC6H4 13 Me H Et H H H H 3-ClC6H4 14 Me H Et H H H H4-ClC6H4 15 Me H Et H H H H 4-MeC6H4 16 Me H Et H H H H 4-t-BuC6H4 17 MeH Et H H H H 1-Naph 18 Me H Et H H H H thiophene-2-yl 19 Me H Et H H H H2-methyl pyridine-5-yl 20 Me H Et Me H H H 4-ClC6H4 21 Me H n-Pr H H H HPh 22 Me H n-Pr H H H H 2-ClC6H4 23 Me H n-Pr H H H H 4-ClC6H4 24 Me Hn-Pr H H H H 4-MeC6H4 25 Me H n-Pr H H H H 4-EtC6H4 26 Me H i-Pr H H H HPh 27 Me H i-Pr H H H H 4-ClC6H4 28 Me H i-Pr H H H H 3,4-Cl2C6H3 29 MeH i-Pr H H H H 2-MeC6H4 30 Me H i-Pr H H H H 4-MeC6H4 31 Me H i-Pr H H HH 4-EtC6H4 32 Me H i-Pr H H H H 2-Naph 33 Me H i-Pr H H H H 5-methylthiophene-2-yl 34 Me H i-Pr H H H H pyridine-3-yl 35 Me H i-Pr Me H H H4-MeC6H4 36 Me H s-Bu H H H H Ph 37 Me H s-Bu H H H H 4-ClC6H4 38 Me Hs-Bu H H H H 3,4-Cl2C6H3 39 Me H s-Bu H H H H 2-MeC6H4 40 Me H s-Bu H HH H 4-MeC6H4 41 Me H s-Bu H H H H 4-t-BuC6H4 42 Me H s-Bu H H H H 1-Naph43 Me H s-Bu H H H H thiophene-2-yl 44 Me H s-Bu H H H Hisothiazole-5-yl 45 Me H s-Bu Me H H H 4-CF3C6H4 46 Me H i-Bu H H H H Ph47 Me H i-Bu H H H H 4-ClC6H4 48 Me H i-Bu H H H H 3,4-Cl2C6H3 49 Me Hi-Bu H H H H 2-MeC6H4 50 Me H i-Bu H H H H 4-MeC6H4 51 Me H i-Bu H H H H4-t-BuC6H4 52 Me H i-Bu H H H H 2-Naph 53 Me H i-Bu H H H Hthiophene-2-yl 54 Me H i-Bu H H H H 3-methyl isothiazole-5-yl 55 Me Hi-Bu Me H H H 4-ClC6H4 56 Me H t-Bu H H H H Ph 57 Me H t-Bu H H H H4-ClC6H4 58 Me H t-Bu H H H H 3,4-Cl2C6H3 59 Me H t-Bu H H H H 2-MeC6H460 Me H t-Bu H H H H 4-MeC6H4 61 Me H t-Bu H H H H 4-t-BuC6H4 62 Me Ht-Bu H H H H 1-Naph 63 Me H t-Bu H H H H thiophene-2-yl 64 Me H t-Bu H HH H isothiazole-5-yl 65 Me H t-Bu Me H H H 4-MeC6H4 66 Me H Ph H H H HPh 67 Me H Ph H H H H 2-ClC6H4 68 Me H Ph H H H H 4-ClC6H4 69 Me H Ph HH H H 4-MeC6H4 70 Me H Ph H H H H 4-EtC6H4 71 Me H 4-ClC6H4 H H H H Ph72 Me H 4-ClC6H4 H H H H 4-CF3C6H4 73 Me H 4-ClC6H4 H H H H 2-MeC6H4 74Me H 4-ClC6H4 H H H H 4-MeC6H4 75 Me H 4-ClC6H4 H H H H 4-t-BuC6H4 76 MeH Bn H H H H Ph 77 Me H Bn H H H H 4-CF3C6H4 78 Me H Bn H H H H 2-MeC6H479 Me H Bn H H H H 4-MeC6H4 80 Me H Bn H H H H 4-EtC6H4 81 Me H -(CH2)2-H H H 4-ClC6H4 82 Me H -(CH2)4- H H H 4-ClC6H4 83 Et H Me H H H H Ph 84Et H Me H H H H 2-ClC6H4 85 Et H Me H Me H H 3-ClC6H4 86 Et H Me H H H H4-ClC6H4 87 Et H Me H H H H 4-MeC6H4 88 Et H Me H H H H 4-t-BuC6H4 89 EtH Me H H H H 1-Naph 90 Et H Me H H H H 5-chloro thiophene-2-yl 91 Et HMe H H H H pyridine-3-yl 92 Et H Me Me H H H 4-ClC6H4 93 Et H Et H H H HPh 94 Et H Et H H H H 2-ClC6H4 95 Et H Et H H H H 3-ClC6H4 96 Et H Et HH H H 4-ClC6H4 97 Et H Et H H H H 4-MeC6H4 98 Et H Et H H H H 4-t-BuC6H499 Et H Et H H H H 1-Naph 100 Et H Et H H H H thiophene-2-yl 101 Et H EtH H H H pyridine-3-yl 102 Et H Et Me H H H 4-ClC6H4 103 Et H i-Pr H H HH Ph 104 Et H i-Pr H H H H 4-ClC6H4 105 Et H i-Pr H H H H 3,4-Cl2C6H3106 Et H i-Pr H H H H 2-MeC6H4 107 Et H i-Pr H H H H 4-MeC6H4 108 Et Hi-Pr H H H H 4-EtC6H4 109 Et H i-Pr H H H H 2-Naph 110 Et H i-Pr H H H Hthiophene-2-yl 111 Et H i-Pr H H H H 4-chloro pyridine-3-yl 112 Et Hi-Pr Me H H H 4-MeC6H4 113 Et H s-Bu H H H H Ph 114 Et H s-Bu H H H H4-ClC6H4 115 Et H s-Bu H H H H 3,4-Cl2C6H3 116 Et H s-Bu H H H H2-MeC6H4 117 Et H s-Bu H H H H 4-MeC6H4 118 Et H s-Bu H H H H 4-t-BuC6H4119 Et H s-Bu H H H H 1-Naph 120 Et H s-Bu H H H H thiophene-2-yl 121 EtH s-Bu H H H H isothiazole-5-yl 122 Et H s-Bu Me H H H 4-MeC6H4 123 Et Hi-Bu H H H H Ph 124 Et H i-Bu H H H H 4-ClC6H4 125 Et H i-Bu H H H H3,4-Cl2C6H3 126 Et H i-Bu H H H H 2-MeC6H4 127 Et H i-Bu H H H H4-MeC6H4 128 Et H i-Bu H H H H 4-t-BuC6H4 129 Et H i-Bu H H H H 1-Naph130 Et H i-Bu H H H H thiophene-2-yl 131 Et H i-Bu H H H Hisothiazole-5-yl 132 Et H i-Bu Me H H H 4-MeC6H4 133 Et H t-Bu H H H HPh 134 Et H t-Bu H H H H 4-ClC6H4 135 Et H t-Bu H H H H 3,4-Cl2C6H3 136Et H t-Bu H H H H 2-MeC6H4 137 Et H t-Bu H H H H 4-MeC6H4 138 Et H t-BuH H H H 4-t-BuC6H4 139 Et H t-Bu H H H H 1-Naph 140 Et H t-Bu H H H Hthiophene-2-yl 141 Et H t-Bu H H H H isothiazole-5-yl 142 Et H t-Bu Me HH H 4-MeC6H4 143 Et H Ph H H H H Ph 144 Et H Ph H H H H 2-ClC6H4 145 EtH Ph H H H H 4-ClC6H4 146 Et H Ph H H H H 4-MeC6H4 147 Et H Ph H H H H4-EtC6H4 148 n-Pr H Me H H H H Ph 149 n-Pr H Me H H H H 2-ClC6H4 150n-Pr H Me Me H H H 3-ClC6H4 151 n-Pr H Me H H H H 4-ClC6H4 152 n-Pr H MeH H H H 4-MeC6H4 153 n-Pr H Me H H H H 4-t-BuC6H4 154 n-Pr H Me H H H H1-Naph 155 n-Pr H Me H H H H 5-ethyl thiophene-2-yl 156 n-Pr H Me H H HH pyridine-3-yl 157 n-Pr H Me Me H H H 4-ClC6H4 158 n-Pr H Et H Et H HPh 159 n-Pr H Et H Et H H 2-ClC6H4 160 n-Pr H Et H Et H H 3-ClC6H4 161n-Pr H Et H Et H H 4-ClC6H4 162 n-Pr H Et H Et H H 4-MeC6H4 163 n-Pr HEt H Et H H 4-t-BuC6H4 164 n-Pr H Et H Et H H 1-Naph 165 n-Pr H Et H EtH H thiophene-2-yl 166 n-Pr H Et H Et H H pyridine-3-yl 167 n-Pr H Et MeEt H H 4-ClC6H4 168 n-Pr H i-Pr H H H H Ph 168 n-Pr H i-Pr H H H H4-ClC6H4 169 n-Pr H i-Pr H H H H 3,4-Cl2C6H3 170 n-Pr H i-Pr H H H H2-MeC6H4 171 n-Pr H i-Pr H H H H 4-MeC6H4 172 n-Pr H i-Pr H H H H4-EtC6H4 173 n-Pr H i-Pr H H H H 2-Naph 174 n-Pr H i-Pr H H H Hthiophene-2-yl 175 n-Pr H i-Pr H H H H 5-methyl pyridine-3-yl 176 n-Pr Hi-Pr Me H H H 4-MeC6H4 177 n-Pr H s-Bu H Me Me H Ph 178 n-Pr H s-Bu H MeMe H 4-ClC6H4 179 n-Pr H s-Bu H Me Me H 3,4-Cl2C6H3 180 n-Pr H s-Bu H MeMe H 2-MeC6H4 181 n-Pr H s-Bu H Me Me H 4-MeC6H4 182 n-Pr H s-Bu H Me MeH 4-t-BuC6H4 183 n-Pr H s-Bu H Me Me H 1-Naph 184 n-Pr H s-Bu H Me Me Hthiophene-2-yl 185 n-Pr H s-Bu H Me Me H isothiazole-5-yl 186 n-Pr Hs-Bu Me Me Me H 4-MeC6H4 187 n-Pr H i-Bu H H H H 4-ClC6H4 188 n-Pr Hi-Bu H H H H 3,4-Cl2C6H3 189 n-Pr H i-Bu H H H H 2-MeC6H4 190 n-Pr Hi-Bu H H H H 4-MeC6H4 191 n-Pr H i-Bu H H H H 4-t-BuC6H4 192 n-Pr H i-BuH H H H 1-Naph 193 n-Pr H i-Bu H H H H thiophene-2-yl 194 n-Pr H i-Bu HH H H isothiazole-5-yl 195 n-Pr H i-Bu Me H H H 4-MeC6H4 196 n-Pr H t-BuH H H H Ph 197 n-Pr H t-Bu H H H H 4-ClC6H4 198 n-Pr H t-Bu H H H H3,4-Cl2C6H3 199 n-Pr H t-Bu H H H H 2-MeC6H4 200 n-Pr H t-Bu H H H H4-MeC6H4 201 n-Pr H t-Bu H H H H 4-t-BuC6H4 202 n-Pr H t-Bu H H H H1-Naph 203 n-Pr H t-Bu H H H H thiophene-2-yl 204 n-Pr H t-Bu H H H Hisothiazole-5-yl 205 n-Pr H t-Bu Me H H H 4-MeC6H4 206 n-Pr H Ph H H H HPh 207 n-Pr H Ph H H H H 2-ClC6H4 208 n-Pr H Ph H H H H 4-ClC6H4 209n-Pr H Ph H H H H 4-MeC6H4 210 n-Pr H Ph H H H H 4-EtC6H4 211 i-Pr H MeH H H H Ph 212 i-Pr H Me H H H H 2-ClC6H4 213 i-Pr H Me H Me H H3-ClC6H4 214 i-Pr H Me H H H H 4-ClC6H4 215 i-Pr H Me H H H H 4-MeC6H4216 i-Pr H Me H H H H 4-t-BuC6H4 217 i-Pr H Me H H H H 1-Naph 218 i-Pr HMe H H H H thiophene-2-yl 219 i-Pr H Me H H H H pyridine-3-yl 220 i-Pr HMe Me H H H 4-ClC6H4 221 i-Pr H Et H H H H Ph 222 i-Pr H Et H H H H2-ClC6H4 223 i-Pr H Et H H H H 3-ClC6H4 224 i-Pr H Et H H H H 4-ClC6H4225 i-Pr H Et H H H H 4-MeC6H4 226 i-Pr H Et H H H H 4-t-BuC6H4 227 i-PrH Et H H H H 1-Naph 228 i-Pr H Et H H H H thiophene-2-yl 229 i-Pr H Et HH H H 2-methyl pyridine-5-yl 230 i-Pr H Et Me H H H 4-ClC6H4 231 i-Pr Hn-Pr H H H H Ph 232 i-Pr H n-Pr H H H H 2-ClC6H4 233 i-Pr H n-Pr H H H H4-ClC6H4 234 i-Pr H n-Pr H H H H 4-MeC6H4 235 i-Pr H n-Pr H H H H4-EtC6H4 236 i-Pr H i-Pr H H H H Ph 237 i-Pr H i-Pr H H H H 4-ClC6H4 238i-Pr H i-Pr H H H H 3,4-Cl2C6H3 239 i-Pr H i-Pr H H H H 2-MeC6H4 240i-Pr H i-Pr H H H H 4-MeC6H4 241 i-Pr H i-Pr H H H H 4-EtC6H4 242 i-Pr Hi-Pr H H H H 2-Naph 243 i-Pr H i-Pr H H H H 5-methyl thiophene-2-yl 244i-Pr H i-Pr H H H H pyridine-3-yl 245 i-Pr H i-Pr Me H H H 4-MeC6H4 246i-Pr H i-Pr H Me H H 4-MeC6H4 247 i-Pr H i-Pr H Me H H 4-ClC6H4 248 i-PrH s-Bu H H H H 3,4-Cl2C6H3 249 i-Pr H s-Bu H H H H 2-MeC6H4 250 i-Pr Hs-Bu H H H H 4-MeC6H4 251 i-Pr H s-Bu H H H H 4-t-BuC6H4 252 i-Pr H s-BuH H H H 1-Naph 253 i-Pr H s-Bu H H H H thiophene-2-yl 254 i-Pr H s-Bu HH H H isothiazole-5-yl 255 i-Pr H s-Bu Me H H H 4-CF3C6H4 256 i-Pr Hi-Bu H H H H Ph 257 i-Pr H i-Bu H H H H 4-ClC6H4 258 i-Pr H i-Bu H H H H3,4-Cl2C6H3 259 i-Pr H i-Bu H H H H 2-MeC6H4 260 i-Pr H i-Bu H H H H4-MeC6H4 261 i-Pr H i-Bu H H H H 4-t-BuC6H4 262 i-Pr H i-Bu H H H H2-Naph 263 i-Pr H i-Bu H H H H thiophene-2-yl 264 i-Pr H i-Bu H H H H3-methyl isothiazole- 5-yl 265 i-Pr H i-Bu Me H H H 4-ClC6H4 266 i-Pr Ht-Bu H H H H Ph 267 i-Pr H t-Bu H H H H 4-ClC6H4 268 i-Pr H t-Bu H H H H3,4-Cl2C6H3 269 i-Pr H t-Bu H H H H 2-MeC6H4 270 i-Pr H t-Bu H H H H4-MeC6H4 271 i-Pr H t-Bu H H H H 4-t-BuC6H4 272 i-Pr H t-Bu H H H H1-Naph 273 i-Pr H t-Bu H H H H thiophene-2-yl 274 i-Pr H t-Bu H H H Hisothiazole-5-yl 275 i-Pr H t-Bu Me H H H 4-MeC6H4 276 i-Pr H Ph H H H HPh 277 i-Pr H Ph H H H H 2-ClC6H4 278 i-Pr H Ph H H H H 4-ClC6H4 279i-Pr H Ph H H H H 4-MeC6H4 280 i-Pr H Ph H H H H 4-EtC6H4 281 i-Pr H4-ClC6H4 H H H H Ph 282 i-Pr H 4-ClC6H4 H H H H 4-CF3C6H4 283 i-Pr H4-ClC6H4 H H H H 2-MeC6H4 284 i-Pr H 4-ClC6H4 H H H H 4-MeC6H4 285 i-PrH 4-ClC6H4 H H H H 4-t-BuC6H4 286 i-Pr H Bn H H H H Ph 287 i-Pr H Bn H HH H 4-CF3C6H4 288 i-Pr H Bn H H H H 2-MeC6H4 289 i-Pr H Bn H H H H4-MeC6H4 290 i-Pr H Bn H H H H 4-ClC6H4 291 i-Pr H -(CH2)4- H H H4-ClC6H4 292 i-Pr H -(CH2)5- H H H 4-ClC6H4 293 s-Bu H Me H H H H Ph 294s-Bu H Me H H H H 2-ClC6H4 295 s-Bu H Me H Me H H 3-ClC6H4 296 s-Bu H MeH H H H 4-ClC6H4 297 s-Bu H Me H H H H 4-MeC6H4 298 s-Bu H Me H H H H4-t-BuC6H4 299 s-Bu H Me H H H H 1-Naph 300 s-Bu H Me H H H H 3-methylthiophene-2-yl 301 s-Bu H Me H H H H pyridine-3-yl 302 s-Bu H Me Me H HH 4-ClC6H4 303 s-Bu Ac Et H H H H Ph 304 s-Bu Ac Et H H H H 2-ClC6H4 305s-Bu Ac Et H H H H 3-ClC6H4 306 s-Bu Ac Et H H H H 4-ClC6H4 307 s-Bu AcEt H H H H 4-MeC6H4 308 s-Bu Ac Et H H H H 4-t-BuC6H4 309 s-Bu Ac Et H HH H 1-Naph 310 s-Bu Ac Et H H H H thiophene-2-yl 311 s-Bu Ac Et H H H Hpyridine-3-yl 312 s-Bu Ac Et Me H H H 4-ClC6H4 313 s-Bu H i-Pr H H H HPh 314 s-Bu H i-Pr H H H H 4-ClC6H4 315 s-Bu H i-Pr H H H H 3,4-Cl2C6H3316 s-Bu H i-Pr H H H H 2-MeC6H4 317 s-Bu H i-Pr H H H H 4-MeC6H4 318s-Bu H i-Pr H H H H 4-EtC6H4 319 s-Bu H i-Pr H H H H 2-Naph 320 s-Bu Hi-Pr H H H H thiophene-2-yl 321 s-Bu H i-Pr H H H H 5-methylpyridine-3-yl 322 s-Bu H i-Pr Me H H H 4-MeC6H4 323 s-Bu H s-Bu H H H BzPh 324 s-Bu H s-Bu H H H Bz 4-ClC6H4 325 s-Bu H s-Bu H H H Bz3,4-Cl2C6H3 326 s-Bu H s-Bu H H H Bz 2-MeC6H4 327 s-Bu H s-Bu H H H Bz4-MeC6H4 328 s-Bu H s-Bu H H H Bz 4-t-BuC6H4 329 s-Bu H s-Bu H H H Bz1-Naph 330 s-Bu H s-Bu H H H Bz thiophene-2-yl 331 s-Bu H s-Bu H H H Bzisothiazole-5-yl 332 s-Bu H s-Bu Me H H Bz 4-MeC6H4 333 s-Bu H i-Bu H HH H Ph 334 s-Bu H i-Bu H H H H 4-ClC6H4 335 s-Bu H i-Bu H H H H3,4-Cl2C6H3 336 s-Bu H i-Bu H H H H 2-MeC6H4 337 s-Bu H i-Bu H H H H4-MeC6H4 338 s-Bu H i-Bu H H H H 4-t-BuC6H4 339 s-Bu H i-Bu H H H H1-Naph 340 s-Bu H i-Bu H H H H thiophene-2-yl 341 s-Bu H i-Bu H H H Hisothiazole-5-yl 342 s-Bu H i-Bu Me H H H 4-MeC6H4 343 s-Bu H t-Bu H H HH Ph 344 s-Bu H t-Bu H H H H 4-ClC6H4 345 s-Bu H t-Bu H H H H3,4-Cl2C6H3 346 s-Bu H t-Bu H H H H 2-MeC6H4 347 s-Bu H t-Bu H H H H4-MeC6H4 348 s-Bu H t-Bu H H H H 4-t-BuC6H4 349 s-Bu H t-Bu H H H H1-Naph 350 s-Bu H t-Bu H H H H thiophene-2-yl 351 s-Bu H t-Bu H H H Hisothiazole-5-yl 352 s-Bu H t-Bu Me H H H 4-MeC6H4 353 s-Bu H Ph H H H HPh 354 s-Bu H Ph H H H H 2-ClC6H4 355 s-Bu H Ph H H H H 4-ClC6H4 356s-Bu H Ph H H H H 4-MeC6H4 357 s-Bu H Ph H H H H 4-EtC6H4 358 i-Bu H MeH H H H Ph 359 i-Bu H Me H H H H 2-ClC6H4 360 i-Bu H Me Me H H H3-ClC6H4 361 i-Bu H Me H H H H 4-ClC6H4 362 i-Bu H Me H H H H 4-MeC6H4363 i-Bu H Me H H H H 4-t-BuC6H4 364 i-Bu H Me H H H H 1-Naph 365 i-Bu HMe H H H H thiophene-2-yl 366 i-Bu H Me H H H H pyridine-3-yl 367 i-Bu HMe Me H H H 4-ClC6H4 368 i-Bu H Et H H H H Ph 369 i-Bu H Et H H H H2-ClC6H4 370 i-Bu H Et H H H H 3-ClC6H4 371 i-Bu H Et H H H H 4-ClC6H4372 i-Bu H Et H H H H 4-MeC6H4 373 i-Bu H Et H H H H 4-t-BuC6H4 374 i-BuH Et H H H H 1-Naph 375 i-Bu H Et H H H H thiophene-2-yl 376 i-Bu H Et HH H H 2-methyl pyridine- 5-yl 377 i-Bu H Et Me H H H 4-ClC6H4 378 i-Bu Hn-Pr H H H H Ph 379 i-Bu H n-Pr H H H H 2-ClC6H4 380 i-Bu H n-Pr H H H H4-ClC6H4 381 i-Bu H n-Pr H H H H 4-MeC6H4 382 i-Bu H n-Pr H H H H4-EtC6H4 383 i-Bu H i-Pr H H H H Ph 384 i-Bu H i-Pr H H H H 4-ClC6H4 385i-Bu H i-Pr H H H H 3,4-Cl2C6H3 386 i-Bu H i-Pr H H H H 2-MeC6H4 387i-Bu H i-Pr H H H H 4-MeC6H4 388 i-Bu H i-Pr H H H H 4-EtC6H4 389 i-Bu Hi-Pr H H H H 2-Naph 390 i-Bu H i-Pr H H H H 5-methyl thiophene- 2-yl 391i-Bu H i-Pr H H H H pyridine-3-yl 392 i-Bu H i-Pr Me H H H 4-MeC6H4 393i-Bu H s-Bu H H H H Ph 394 i-Bu H s-Bu H H H H 4-ClC6H4 395 i-Bu H s-BuH H H H 3,4-Cl2C6H3 396 i-Bu H s-Bu H H H H 2-MeC6H4 397 i-Bu H s-Bu H HH H 4-MeC6H4 398 i-Bu H s-Bu H H H H 4-t-BuC6H4 399 i-Bu H s-Bu H H H H1-Naph 400 i-Bu H s-Bu H H H H thiophene-2-yl 401 i-Bu H s-Bu H H H Hisothiazole-5-yl 402 i-Bu H s-Bu Me H H H 4-CF3C6H4 403 i-Bu H i-Bu H HH H Ph 404 i-Bu H i-Bu H H H H 4-ClC6H4 405 i-Bu H i-Bu H H H H3,4-Cl2C6H3 406 i-Bu H i-Bu H H H H 2-MeC6H4 407 i-Bu H i-Bu H H H H4-MeC6H4 408 i-Bu H i-Bu H H H H 4-t-BuC6H4 409 i-Bu H i-Bu H H H H2-Naph 410 i-Bu H i-Bu H H H H thiophene-2-yl 411 i-Bu H i-Bu H H H H3-methyl isothiazole-5-yl 412 i-Bu H i-Bu Me H H H 4-ClC6H4 413 i-Bu Ht-Bu H H H H Ph 414 i-Bu H t-Bu H H H H 4-ClC6H4 415 i-Bu H t-Bu H H H H3,4-Cl2C6H3 416 i-Bu H t-Bu H H H H 2-MeC6H4 417 i-Bu H t-Bu H H H H4-MeC6H4 418 i-Bu H t-Bu H H H H 4-t-BuC6H4 419 i-Bu H t-Bu H H H H1-Naph 420 i-Bu H t-Bu H H H H thiophene-2-yl 421 i-Bu H t-Bu H H H Hisothiazole-5-yl 422 i-Bu H t-Bu Me H H H 4-MeC6H4 423 i-Bu H Ph H H H HPh 424 i-Bu H Ph H H H H 2-ClC6H4 425 i-Bu H Ph H H H H 4-ClC6H4 426i-Bu H Ph H H H H 4-MeC6H4 427 i-Bu H Ph H H H H 4-EtC6H4 428 i-Bu H4-ClC6H4 H H H H Ph 429 i-Bu H 4-ClC6H4 H H H H 4-CF3C6H4 430 i-Bu H4-ClC6H4 H H H H 2-MeC6H4 431 i-Bu H 4-ClC6H4 H H H H 4-MeC6H4 432 i-BuH 4-ClC6H4 H H H H 4-t-BuC6H4 433 i-Bu H Bn H H H H Ph 434 i-Bu H Bn H HH H 4-CF3C6H4 435 i-Bu H Bn H H H H 2-MeC6H4 436 i-Bu H Bn H H H H4-MeC6H4 437 i-Bu H Bn H H H H 4-EtC6H4 438 i-Bu H -(CH2)4- H H H4-ClC6H4 439 i-Bu H -(CH2)5- H H H 4-ClC6H4 440 t-Bu H Me H H H H Ph 441t-Bu H Me H H H H 2-ClC6H4 442 t-Bu H Me H Et H H 3-ClC6H4 443 t-Bu H MeH H H H 4-ClC6H4 444 t-Bu H Me H H H H 4-MeC6H4 445 t-Bu H Me H H H H4-t-BuC6H4 446 t-Bu H Me H H H H 1-Naph 447 t-Bu H Me H H H H 5-methylthiophene-2-yl 448 t-Bu H Me H H H H pyridine-3-yl 449 t-Bu H Me Me H HH 4-ClC6H4 450 t-Bu Me Et H H H H Ph 451 t-Bu Me Et H H H H 2-ClC6H4 452t-Bu Me Et H H H H 3-ClC6H4 453 t-Bu Me Et H H H H 4-ClC6H4 454 t-Bu MeEt H H H H 4-MeC6H4 455 t-Bu Me Et H H H H 4-t-BuC6H4 456 t-Bu Me Et H HH H 1-Naph 457 t-Bu Me Et H H H H thiophene-2-yl 458 t-Bu Me Et H H H Hpyridine-3-yl 459 t-Bu Me Et Me H H H 4-ClC6H4 460 t-Bu H i-Pr H H H HPh 461 t-Bu H i-Pr H H H H 4-ClC6H4 462 t-Bu H i-Pr H H H H 3,4-Cl2C6H3463 t-Bu H i-Pr H H H H 2-MeC6H4 464 t-Bu H i-Pr H H H H 4-MeC6H4 465t-Bu H i-Pr H H H H 4-EtC6H4 466 t-Bu H i-Pr H H H H 2-Naph 467 t-Bu Hi-Pr H H H H thiophene-2-yl 468 t-Bu H i-Pr H H H H 5-methylpyridine-3-yl 469 t-Bu H i-Pr Me H H H 4-MeC6H4 470 t-Bu H i-Pr H Me H H4-MeC6H4 471 t-Bu H i-Pr H Me H H 4-ClC6H4 472 t-Bu H s-Bu H H H Et3,4-Cl2C6H3 473 t-Bu H s-Bu H H H Et 2-MeC6H4 474 t-Bu H s-Bu H H H Et4-MeC6H4 475 t-Bu H s-Bu H H H Et 4-t-BuC6H4 476 t-Bu H s-Bu H H H Et1-Naph 478 t-Bu H s-Bu H H H Et thiophene-2-yl 479 t-Bu H s-Bu H H H Etisothiazole-5-yl 480 t-Bu H s-Bu Me H H Et 4-MeC6H4 481 t-Bu H i-Bu H HH H Ph 482 t-Bu H i-Bu H H H H 4-ClC6H4 483 t-Bu H i-Bu H H H H3,4-Cl2C6H3 484 t-Bu H i-Bu H H H H 2-MeC6H4 485 t-Bu H i-Bu H H H H4-MeC6H4 486 t-Bu H i-Bu H H H H 4-t-BuC6H4 487 t-Bu H i-Bu H H H H1-Naph 488 t-Bu H i-Bu H H H H thiophene-2-yl 489 t-Bu H i-Bu H H H Hisothiazole-5-yl 490 t-Bu H i-Bu Me H H H 4-MeC6H4 491 t-Bu H t-Bu H H HH Ph 492 t-Bu H t-Bu H H H H 4-ClC6H4 493 t-Bu H t-Bu H H H H3,4-Cl2C6H3 494 t-Bu H t-Bu H H H H 2-MeC6H4 495 t-Bu H t-Bu H H H H4-MeC6H4 496 t-Bu H t-Bu H H H H 4-t-BuC6H4 497 t-Bu H t-Bu H H H H1-Naph 498 t-Bu H t-Bu H H H H thiophene-2-yl 499 t-Bu H t-Bu H H H Hisothiazole-5-yl 500 t-Bu H t-Bu Me H H H 4-MeC6H4 501 t-Bu H Ph H H H HPh 502 t-Bu H Ph H H H H 2-ClC6H4 503 t-Bu H Ph H H H H 4-ClC6H4 504t-Bu H Ph H H H H 4-MeC6H4 505 t-Bu H Ph H H H H 4-EtC6H4 506 Ph H Me HH H H Ph 507 Ph H Me H H H H 2-ClC6H4 508 Ph H Me Me H H H 3-ClC6H4 509Ph H Me H H H H 4-ClC6H4 510 Ph H Me H H H H 4-MeC6H4 511 Ph H Me H H HH 4-t-BuC6H4 512 Ph H Me H H H H 1-Naph 513 Ph H Me H H H H 5-methylthiophene-2-yl 514 Ph H Me H H H H pyridine-3-yl 515 Ph H Me Me H H H4-ClC6H4 516 Ph H Et H H H H Ph 517 Ph H Et H H H H 2-ClC6H4 518 Ph H EtH H H H 3-ClC6H4 519 Ph H Et H H H H 4-ClC6H4 520 Ph H Et H H H H4-MeC6H4 521 Ph H Et H H H H 4-t-BuC6H4 522 Ph H Et H H H H 1-Naph 523Ph H Et H H H H thiophene-2-yl 524 Ph H Et H H H H pyridine-3-yl 525 PhH Et Me H H H 4-ClC6H4 526 Ph H i-Pr H H H H Ph 527 Ph H i-Pr H H H H4-ClC6H4 528 Ph H i-Pr H H H H 3,4-Cl2C6H3 529 Ph H i-Pr H H H H2-MeC6H4 530 Ph H i-Pr H H H H 4-MeC6H4 531 Ph H i-Pr H H H H 4-EtC6H4532 Ph H i-Pr H H H H 2-Naph 533 Ph H i-Pr H H H H thiophene-2-yl 534 PhH i-Pr H H H H 5-methyl pyridine-3-yl 535 Ph H i-Pr Me H H H 4-MeC6H4536 Ph H allyl H H H H Ph 537 Ph H allyl H H H H 4-ClC6H4 538 Ph H allylH H H H 3,4-Cl2C6H3 539 Ph H allyl H H H H 2-MeC6H4 540 Ph H allyl H H HH 4-MeC6H4 541 Ph H allyl H H H H 4-t-BuC6H4 542 Ph H allyl H H H H1-Naph 543 Ph H allyl H H H H thiophene-2-yl 544 Ph H allyl H H H Hisothiazole-5-yl 545 Ph H allyl Me H H H 4-MeC6H4 546 Ph H i-Bu H H H HPh 547 Ph H i-Bu H H H H 4-ClC6H4 548 Ph H i-Bu H H H H 3,4-Cl2C6H3 549Ph H i-Bu H H H H 2-MeC6H4 550 Ph H i-Bu H H H H 4-MeC6H4 551 Ph H i-BuH H H H 4-t-BuC6H4 552 Ph H i-Bu H H H H 1-Naph 553 Ph H i-Bu H H H Hthiophene-2-yl 554 Ph H i-Bu H H H H isothiazole-5-yl 555 Ph H i-Bu Me HH H 4-MeC6H4 556 Ph H propargyl H H H H Ph 557 Ph H propargyl H H H H4-ClC6H4 558 Ph H propargyl H H H H 3,4-Cl2C6H3 559 Ph H propargyl H H HH 2-MeC6H4 560 Ph H propargyl H H H H 4-MeC6H4 561 Ph H propargyl H H HH 4-t-BuC6H4 562 Ph H propargyl H H H H 1-Naph 563 Ph H propargyl H H HH thiophene-2-yl 564 Ph H propargyl H H H H isothiazole-5-yl 565 Ph Hpropargyl Me H H H 4-MeC6H4 566 Ph H Ph H H H H Ph 567 Ph H Ph H H H H2-ClC6H4 568 Ph H Ph H H H H 4-ClC6H4 569 Ph H Ph H H H H 4-MeC6H4 570Ph H Ph H H H H 4-EtC6H4 571 Bn H Me H H H H Ph 572 Bn H Me H H H H2-ClC6H4 573 Bn H Me H Me H H 3-ClC6H4 574 Bn H Me H H H H 4-ClC6H4 575Bn H Me H H H H 4-MeC6H4 576 Bn H Me H H H H 4-t-BuC6H4 577 Bn H Me H HH H 1-Naph 578 Bn H Me H H H H thiophene-2-yl 579 Bn H Me H H H Hpyridine-3-yl 580 Bn H Me Me H H H 4-ClC6H4 581 Bn H Et H H H H Ph 582Bn H Et H H H H 2-ClC6H4 583 Bn H Et H H H H 3-ClC6H4 584 Bn H Et H H HH 4-ClC6H4 585 Bn H Et H H H H 4-MeC6H4 586 Bn H Et H H H H 4-t-BuC6H4587 Bn H Et H H H H 1-Naph 588 Bn H Et H H H H thiophene-2-yl 589 Bn HEt H H H H 4-methyl pyridine-5-yl 590 Bn H Et Me H H H 4-ClC6H4 591 Bn Hn-Pr H H H H Ph 592 Bn H n-Pr H H H H 2-ClC6H4 593 Bn H n-Pr H H H H4-ClC6H4 594 Bn H n-Pr H H H H 4-MeC6H4 595 Bn H n-Pr H H H H 4-EtC6H4596 Bn H i-Pr H H H H Ph 597 Bn H i-Pr H H H H 4-ClC6H4 598 Bn H i-Pr HH H H 3,4-Cl2C6H3 599 Bn H i-Pr H H H H 2-MeC6H4 600 Bn H i-Pr H H H H4-MeC6H4 601 Bn H i-Pr H H H H 4-EtC6H4 602 Bn H i-Pr H H H H 2-Naph 603Bn H i-Pr H H H H 5-methyl thiophene-2-yl 604 Bn H i-Pr H H H Hpyridine-3-yl 605 Bn H i-Pr Me H H H 4-MeC6H4 606 Bn H s-Bu H H H H Ph607 Bn H s-Bu H H H H 4-ClC6H4 608 Bn H s-Bu H H H H 3,4-Cl2C6H3 609 BnH s-Bu H H H H 2-MeC6H4 610 Bn H s-Bu H H H H 4-MeC6H4 611 Bn H s-Bu H HH H 4-t-BuC6H4 612 Bn H s-Bu H H H H 1-Naph 613 Bn H s-Bu H H H Hthiophene-2-yl 614 Bn H s-Bu H H H H isothiazole-5-yl 615 Bn H s-Bu Me HH H 4-CF3C6H4 616 Bn H i-Bu H H H H Ph 617 Bn H i-Bu H H H H 4-ClC6H4618 Bn H i-Bu H H H H 3,4-Cl2C6H3 619 Bn H i-Bu H H H H 2-MeC6H4 620 BnH i-Bu H H H H 4-MeC6H4 621 Bn H i-Bu H H H H 4-t-BuC6H4 622 Bn H i-Bu HH H H 2-Naph 623 Bn H i-Bu H H H H thiophene-2-yl 624 Bn H i-Bu H H H H3-methyl isothiazole-5-yl 625 Bn H i-Bu Me H H H 4-ClC6H4 626 Bn H t-BuH H H H Ph 627 Bn H t-Bu H H H H 4-ClC6H4 628 Bn H t-Bu H H H H3,4-Cl2C6H3 629 Bn H t-Bu H H H H 2-MeC6H4 630 Bn H t-Bu H H H H4-MeC6H4 631 Bn H t-Bu H H H H 4-t-BuC6H4 632 Bn H t-Bu H H H H 1-Naph633 Bn H t-Bu H H H H thiophene-2-yl 634 Bn H t-Bu H H H Hisothiazole-5-yl 635 Bn H t-Bu Me H H H 4-MeC6H4 636 Bn H Ph H H H H Ph637 Bn H Ph H H H H 2-ClC6H4 638 Bn H Ph H H H H 4-ClC6H4 639 Bn H Ph HH H H 4-MeC6H4 640 Bn H Ph H H H H 4-EtC6H4 641 Bn H 4-MeC6H4 H H H H Ph642 Bn H 4-MeC6H4 H H H H 4-CF3C6H4 643 Bn H 4-MeC6H4 H H H H 2-MeC6H4644 Bn H 4-MeC6H4 H H H H 4-MeC6H4 645 Bn H 4-MeC6H4 H H H H 4-t-BuC6H4646 Bn H Bn H H H H Ph 647 Bn H Bn H H H H 4-CF3C6H4 648 Bn H Bn H H H H2-MeC6H4 649 Bn H Bn H H H H 4-MeC6H4 650 Bn H Bn H H H H 4-EtC6H4 651Bn H -(CH2)4- H H H 4-ClC6H4 652 Bn H -(CH2)5- H H H 4-ClC6H4 653 2-NaphH Me H H H H Ph 654 2-Naph H Me H H H H 2-BrC6H4 655 2-Naph H Me Me H HH 3-BrC6H4 656 2-Naph H Me H H H H 4-BrC6H4 657 2-Naph H Me H H H H4-MeC6H4 658 2-Naph H Me H H H H 4-t-BuC6H4 659 2-Naph H Me H H H H1-Naph 660 2-Naph H Me H H H H 5-methyl thiophene-2-yl 661 2-Naph H Me HH H H pyridine-3-yl 662 2-Naph H Me Me H H H 4-ClC6H4 663 2-Naph H Et HH H H Ph 664 2-Naph H Et H H H H 2-FC6H4 665 2-Naph H Et H H H H 3-FC6H4666 2-Naph H Et H H H H 4-FC6H4 667 2-Naph H Et H H H H 4-MeC6H4 6682-Naph H Et H H H H 4-t-BuC6H4 669 2-Naph H Et H H H H 1-Naph 670 2-NaphH Et H H H H thiophene-2-yl 671 2-Naph H Et H H H H pyridine-3-yl 6722-Naph H Et Me H H H 4-ClC6H4 673 2-Naph H i-Pr H H H H Ph 674 2-Naph Hi-Pr H H H H 4-ClC6H4 675 2-Naph H i-Pr H H H H 3,4-Cl2C6H3 676 2-Naph Hi-Pr H H H H 2-MeC6H4 677 2-Naph H i-Pr H H H H 4-MeC6H4 678 2-Naph Hi-Pr H H H H 4-EtC6H4 679 2-Naph H i-Pr H H H H 2-Naph 680 2-Naph H i-PrH H H H thiophene-2-yl 681 2-Naph H i-Pr H H H H 5-methyl pyridine- 3-yl682 2-Naph H i-Pr Me H H H 4-MeC6H4 683 2-Naph H s-Bu H H H H Ph 6842-Naph H s-Bu H H H H 4-ClC6H4 685 2-Naph H s-Bu H H H H 3,4-Cl2C6H3 6862-Naph H s-Bu H H H H 2-MeC6H4 687 2-Naph H s-Bu H H H H 4-MeC6H4 6882-Naph H s-Bu H H H H 4-t-BuC6H4 689 2-Naph H s-Bu H H H H 1-Naph 6902-Naph H s-Bu H H H H thiophene-2-yl 691 2-Naph H s-Bu H H H Hisothiazole-5-yl 692 2-Naph H s-Bu Me H H H 4-MeC6H4 693 2-Naph H i-Bu HH H H Ph 694 2-Naph H i-Bu H H H H 4-ClC6H4 695 2-Naph H i-Bu H H H H3,4-Cl2C6H3 696 2-Naph H i-Bu H H H H 2-MeC6H4 697 2-Naph H i-Bu H H H H4-MeC6H4 698 2-Naph H i-Bu H H H H 4-t-BuC6H4 699 2-Naph H i-Bu H H H H1-Naph 700 2-Naph H i-Bu H H H H thiophene-2-yl 701 2-Naph H i-Bu H H HH isothiazole-5-yl 702 2-Naph H i-Bu Me H H H 4-MeC6H4 703 2-Naph Hc-Hex H H H H Ph 704 2-Naph H c-Hex H H H H 4-ClC6H4 705 2-Naph H c-HexH H H H 3,4-Cl2C6H3 706 2-Naph H c-Hex H H H H 2-MeC6H4 707 2-Naph Hc-Hex H H H H 4-MeC6H4 708 2-Naph H c-Hex H H H H 4-t-BuC6H4 709 2-NaphH c-Hex H H H H 1-Naph 710 2-Naph H c-Hex H H H H thiophene-2-yl 7112-Naph H c-Hex H H H H isothiazole-5-yl 712 2-Naph H c-Hex Me H H H4-MeC6H4 713 2-Naph H Ph H H H H Ph 714 2-Naph H Ph H H H H 2-ClC6H4 7152-Naph H Ph H H H H 4-ClC6H4 716 2-Naph H Ph H H H H 4-MeC6H4 717 2-NaphH Ph H H H H 4-EtC6H4 718 allyl H Me H H H H Ph 719 allyl H Me H H H H2-ClC6H4 720 allyl H Me Me H H H 3-ClC6H4 721 allyl H Me H H H H4-ClC6H4 722 allyl H Me H H H H 4-CNC6H4 723 allyl H Me H H H H4-t-BuC6H4 724 allyl H Me H H H H 1-Naph 725 allyl H Me H H H H 5-methylthiophene-2-yl 726 allyl H Me H H H H pyridine-3-yl 727 allyl H Me Me HH H 4-CF3C6H4 728 allyl H Et H H H H Ph 729 allyl H Et H H H H 2-ClC6H4730 allyl H Et H H H H 3-ClC6H4 731 allyl H Et H H H H 4-ClC6H4 732allyl H Et H H H H 4-MeC6H4 733 allyl H Et H H H H 4-t-BuC6H4 734 allylH Et H H H H 1-Naph 735 allyl H Et H H H H thiophene-2-yl 736 allyl H EtH H H H pyridine-3-yl 737 allyl H Et Me H H H 4-ClC6H4 738 allyl H i-PrH H H H Ph 739 allyl H i-Pr H H H H 4-ClC6H4 740 allyl H i-Pr H H H H3,4-Cl2C6H3 741 allyl H i-Pr H H H H 2-MeC6H4 742 allyl H i-Pr H H H H4-MeC6H4 743 allyl H i-Pr H H H H 4-EtC6H4 744 allyl H i-Pr H H H H2-Naph 745 allyl H i-Pr H H H H thiophene-2-yl 746 allyl H i-Pr H H H H5-methyl pyridine-3-yl 747 allyl H i-Pr Me H H H 4-MeC6H4 748 allyl Hs-Bu H H H H Ph 749 allyl H s-Bu H H H H 4-ClC6H4 750 allyl H s-Bu H H HH 3,4-Cl2C6H3 751 allyl H s-Bu H H H H 2-MeC6H4 752 allyl H s-Bu H H H H4-MeC6H4 753 allyl H s-Bu H H H H 4-t-BuC6H4 754 allyl H s-Bu H H H H1-Naph 755 allyl H s-Bu H H H H thiophene-2-yl 756 allyl H s-Bu H H H Hisothiazole-5-yl 757 allyl H s-Bu Me H H H 4-MeC6H4 758 allyl H i-Bu H HH H Ph 759 allyl H i-Bu H H H H 4-ClC6H4 760 allyl H i-Bu H H H H3,4-Cl2C6H3 761 allyl H i-Bu H H H H 2-MeC6H4 762 allyl H i-Bu H H H H4-MeC6H4 763 allyl H i-Bu H H H H 4-t-BuC6H4 764 allyl H i-Bu H H H H1-Naph 765 allyl H i-Bu H H H H thiophene-2-yl 766 allyl H i-Bu H H H Hisothiazole-5-yl 767 allyl H i-Bu Me H H H 4-MeC6H4 768 allyl H t-Bu H HH H Ph 769 allyl H t-Bu H H H H 4-ClC6H4 770 allyl H t-Bu H H H H3,4-Cl2C6H3 771 allyl H t-Bu H H H H 2-MeC6H4 772 allyl H t-Bu H H H H4-MeC6H4 773 allyl H t-Bu H H H H 4-t-BuC6H4 774 allyl H t-Bu H H H H1-Naph 775 allyl H t-Bu H H H H thiophene-2-yl 776 allyl H t-Bu H H H Hisothiazole-5-yl 777 allyl H t-Bu Me H H H 4-MeC6H4 778 allyl H Ph H H HH Ph 779 allyl H Ph H H H H 2-ClC6H4 780 allyl H 4-FC6H4 H H H H4-ClC6H4 781 allyl H Ph H H H H 4-MeC6H4 782 allyl H 4-BrC6H4 H H H H4-EtC6H4 783 propargyl H Me H H H H Ph 784 propargyl H Me H H H H2-IC6H4 785 propargyl H Me H Me Me H 3-IC6H4 786 propargyl H Me H H H H4-IC6H4 787 propargyl H Me H H H H 4-MeC6H4 788 propargyl H Me H H H H4-t-BuC6H4 789 propargyl H Me H H H H 1-Naph 790 propargyl H Me H H H H5-methyl thiophene-2-yl 791 propargyl H Me H H H H pyridine-3-yl 792propargyl H Me Me H H H 4-ClC6H4 793 propargyl H Et H H H H Ph 794propargyl H Et H H H H 2-ClC6H4 795 propargyl H Et H H H H 3-ClC6H4 796propargyl H Et H H H H 4-ClC6H4 797 propargyl H Et H H H H 4-MeC6H4 798propargyl H Et H H H H 4-t-BuC6H4 799 propargyl H Et H H H H 1-Naph 800propargyl H Et H H H H thiophene-2-yl 801 propargyl H Et H H H Hpyridine-3-yl 802 propargyl H Et Me H H H 4-ClC6H4 803 propargyl H i-PrH H H H Ph 804 propargyl H i-Pr H H H H 4-ClC6H4 805 propargyl H i-Pr HH H H 3,4-Cl2C6H3 806 propargyl H i-Pr H H H H 2-MeC6H4 807 propargyl Hi-Pr H H H H 4-MeC6H4 808 propargyl H i-Pr H H H H 4-EtC6H4 809propargyl H i-Pr H H H H 2-Naph 810 propargyl H i-Pr H H H Hthiophene-2-yl 811 propargyl H i-Pr H H H H 5-methyl pyridine-3-yl 812propargyl H i-Pr Me H H H 4-MeC6H4 813 propargyl H s-Bu H H H H Ph 814propargyl H s-Bu H H H H 4-ClC6H4 815 propargyl H s-Bu H H H H3,4-Cl2C6H3 816 propargyl H s-Bu H H H H 2-MeC6H4 817 propargyl H s-Bu HH H H 4-MeC6H4 818 propargyl H s-Bu H H H H 4-t-BuC6H4 819 propargyl Hs-Bu H H H H 1-Naph 820 propargyl H s-Bu H H H H thiophene-2-yl 821propargyl H s-Bu H H H H isothiazole-5-yl 822 propargyl H s-Bu Me H H H4-MeC6H4 823 propargyl H i-Bu H H H H Ph 824 propargyl H i-Bu H H H H4-ClC6H4 825 propargyl H i-Bu H H H H 3,4-Cl2C6H3 826 propargyl H i-Bu HH H H 2-MeC6H4 827 propargyl H i-Bu H H H H 4-MeC6H4 828 propargyl Hi-Bu H H H H 4-t-BuC6H4 829 propargyl H i-Bu H H H H 1-Naph 830propargyl H i-Bu H H H H thiophene-2-yl 831 propargyl H i-Bu H H H Hisothiazole-5-yl 832 propargyl H i-Bu Me H H H 4-MeC6H4 833 propargyl Ht-Bu H H H H Ph 834 propargyl H t-Bu H H H H 4-ClC6H4 835 propargyl Ht-Bu H H H H 3,4-Cl2C6H3 836 propargyl H t-Bu H H H H 2-MeC6H4 837propargyl H t-Bu H H H H 4-MeC6H4 838 propargyl H t-Bu H H H H4-t-BuC6H4 839 propargyl H t-Bu H H H H 1-Naph 840 propargyl H t-Bu H HH H thiophene-2-yl 841 propargyl H t-Bu H H H H isothiazole-5-yl 842propargyl H t-Bu Me H H H 4-MeC6H4 843 propargyl H Ph H Bn H H Ph 844propargyl H Ph H H H H 2-ClC6H4 845 propargyl H 4-ClC6H4 H H H H4-ClC6H4 846 propargyl H Ph H H H H 4-MeC6H4 847 propargyl H 4-MeC6H4 HH H H 4-EtC6H4 848 c-Pr H Me H H H H Ph 849 c-Pr H Me H H H H 2-ClC6H4850 c-Pr H Me Me H H H 3-ClC6H4 851 c-Pr H Me H H H H 4-ClC6H4 852 c-PrH Me H H H H 4-MeC6H4 853 c-Pr H Me H H H H 4-t-BuC6H4 854 c-Pr H Me H HH H 1-Naph 855 c-Pr H Me H H H H 5-methyl thiophene-2-yl 856 c-Pr H Me HH H H pyridine-3-yl 857 c-Pr H Me Me H H H 4-ClC6H4 858 c-Pr H Et H H HH Ph 859 c-Pr H Et H H H H 2-ClC6H4 860 c-Pr H Et H H H H 3-ClC6H4 861c-Pr H Et H H H H 4-ClC6H4 862 c-Pr H Et H H H H 4-MeC6H4 863 c-Pr H EtH H H H 4-t-BuC6H4 864 c-Pr H Et H H H H 1-Naph 865 c-Pr H Et H H H Hthiophene-2-yl 866 c-Pr H Et H H H H pyridine-3-yl 867 c-Pr H Et Me H HH 4-ClC6H4 868 c-Pr H i-Pr H H H H Ph 869 c-Pr H i-Pr H H H H 4-ClC6H4870 c-Pr H i-Pr H H H H 3,4-Cl2C6H3 871 c-Pr H i-Pr H H H H 2-MeC6H4 872c-Pr H i-Pr H H H H 4-MeC6H4 873 c-Pr H i-Pr H H H H 4-EtC6H4 874 c-Pr Hi-Pr H H H H 2-Naph 875 c-Pr H i-Pr H H H H thiophene-2-yl 876 c-Pr Hi-Pr H H H H 5-methyl pyridine-3-yl 878 c-Pr H i-Pr Me H H H 4-MeC6H4879 c-Pr H s-Bu H H H H Ph 880 c-Pr H s-Bu H H H H 4-ClC6H4 881 c-Pr Hs-Bu H H H H 3,4-Cl2C6H3 882 c-Pr H s-Bu H H H H 2-MeC6H4 883 c-Pr Hs-Bu H H H H 4-MeC6H4 884 c-Pr H s-Bu H H H H 4-t-BuC6H4 885 c-Pr H s-BuH H H H 1-Naph 886 c-Pr H s-Bu H H H H thiophene-2-yl 887 c-Pr H s-Bu HH H H isothiazole-5-yl 888 c-Pr H s-Bu Me H H H 4-MeC6H4 889 c-Pr H i-BuH H H H Ph 890 c-Pr H i-Bu H H H H 4-ClC6H4 891 c-Pr H i-Bu H H H H3,4-Cl2C6H3 892 c-Pr H i-Bu H H H H 2-MeC6H4 893 c-Pr H i-Bu H H H H4-MeC6H4 894 c-Pr H i-Bu H H H H 4-t-BuC6H4 895 c-Pr H i-Bu H H H H1-Naph 896 c-Pr H i-Bu H H H H thiophene-2-yl 897 c-Pr H i-Bu H H H Hisothiazole-5-yl 898 c-Pr H i-Bu Me H H H 4-MeC6H4 899 c-Pr H t-Bu H BnH H Ph 900 c-Pr H t-Bu H H H H 4-ClC6H4 901 c-Pr H t-Bu H H H H3,4-Cl2C6H3 902 c-Pr H t-Bu H H H H 2-MeC6H4 903 c-Pr H t-Bu H H H H4-MeC6H4 904 c-Pr H t-Bu H H H H 4-t-BuC6H4 905 c-Pr H t-Bu H H H H1-Naph 906 c-Pr H t-Bu H H H H thiophene-2-yl 907 c-Pr H t-Bu H H H Hisothiazole-5-yl 908 c-Pr H t-Bu Me H H H 4-MeC6H4 909 c-Pr H Ph H H H HPh 910 c-Pr H Ph H H H H 2-ClC6H4 911 c-Pr H Ph H H H H 4-ClC6H4 912c-Pr H Ph H H H H 4-MeC6H4 913 c-Pr H Ph H H H H 4-EtC6H4 914 c-Hex H MeH H H H Ph 915 c-Hex H Me H H H H 2-ClC6H4 916 c-Hex H Me H Et H H3-ClC6H4 917 c-Hex H Me H H H H 4-ClC6H4 918 c-Hex H Me H H H H 4-MeC6H4919 c-Hex H Me H H H H 4-t-BuC6H4 920 c-Hex H Me H H H H 1-Naph 921c-Hex H Me H H H H 5-methyl thiophene-2-yl 922 c-Hex H Me H H H Hpyridine-3-yl 923 c-Hex H Me Me H H H 4-ClC6H4 924 c-Hex H Et H H H H Ph925 c-Hex H Et H H H H 2-ClC6H4 926 c-Hex H Et H H H H 3-ClC6H4 927c-Hex H Et H H H H 4-ClC6H4 928 c-Hex H Et H H H H 4-MeC6H4 929 c-Hex HEt H H H H 4-t-BuC6H4 930 c-Hex H Et H H H H 1-Naph 931 c-Hex H Et H H HH thiophene-2-yl 932 c-Hex H Et H H H H pyridine-3-yl 933 c-Hex H Et MeH H H 4-ClC6H4 934 c-Hex H i-Pr H H H H Ph 935 c-Hex H i-Pr H H H H4-ClC6H4 936 c-Hex H i-Pr H H H H 3,4-Cl2C6H3 937 c-Hex H i-Pr H H H H2-MeC6H4 938 c-Hex H i-Pr H H H H 4-MeC6H4 939 c-Hex H i-Pr H H H H4-EtC6H4 940 c-Hex H i-Pr H H H H 2-Naph 941 c-Hex H i-Pr H H H Hthiophene-2-yl 942 c-Hex H i-Pr H H H H 5-methyl pyridine-3-yl 943 c-HexH i-Pr Me H H H 4-MeC6H4 944 c-Hex H s-Bu H H H H Ph 945 c-Hex H s-Bu HH H H 4-ClC6H4 946 c-Hex H s-Bu H H H H 3,4-Cl2C6H3 947 c-Hex H s-Bu H HH H 2-MeC6H4 948 c-Hex H s-Bu H H H H 4-MeC6H4 949 c-Hex H s-Bu H H H H4-t-BuC6H4 950 c-Hex H s-Bu H Ph H H 1-Naph 951 c-Hex H s-Bu H H H Hthiophene-2-yl 952 c-Hex H s-Bu H H H H isothiazole-5-yl 953 c-Hex Hs-Bu Me H H H 4-MeC6H4 954 c-Hex H i-Bu H H H H Ph 955 c-Hex H i-Bu H HH H 4-ClC6H4 956 c-Hex H i-Bu H H H H 3,4-Cl2C6H3 957 c-Hex H i-Bu H H HH 2-MeC6H4 958 c-Hex H i-Bu H H H H 4-MeC6H4 959 c-Hex H i-Bu H H H H4-t-BuC6H4 960 c-Hex H i-Bu H H H H 1-Naph 961 c-Hex H i-Bu H H H Hthiophene-2-yl 962 c-Hex H i-Bu H H H H isothiazole-5-yl 963 c-Hex Hi-Bu Me H H H 4-MeC6H4 964 c-Hex H t-Bu H H H H Ph 965 c-Hex H t-Bu H HH H 4-ClC6H4 966 c-Hex H t-Bu H H H H 3,4-Cl2C6H3 967 c-Hex H t-Bu H H HH 2-MeC6H4 968 c-Hex H t-Bu H H H H 4-MeC6H4 969 c-Hex H t-Bu H H H H4-t-BuC6H4 970 c-Hex H t-Bu H H H H 1-Naph 971 c-Hex H t-Bu H H H Hthiophene-2-yl 972 c-Hex H t-Bu H H H H isothiazole-5-yl 973 c-Hex Ht-Bu Me H H H 4-MeC6H4 974 c-Hex H Ph H H H H Ph 975 c-Hex H Ph H H H H2-ClC6H4 976 c-Hex H Ph H H H H 4-ClC6H4 977 c-Hex H Ph H H H H 4-MeC6H4978 c-Hex H Ph H H H H 4-EtC6H4 979 vinyl H Me H H H H Ph 980 vinyl H MeH H H H 2-ClC6H4 981 vinyl H Me Me H H H 3-ClC6H4 982 vinyl H Me H H H H4-ClC6H4 983 vinyl H Me H H H H 4-MeC6H4 984 vinyl H Me H H H H4-t-BuC6H4 985 vinyl H Me H H H H 1-Naph 986 vinyl H Me H H H H 5-ethylthiophene-2-yl 987 vinyl H Me H H H H pyridine-3-yl 988 vinyl H Me Me HH H 4-ClC6H4 989 vinyl H Et H H H H Ph 990 vinyl H Et H H H H 2-ClC6H4991 vinyl H Et H H H H 3-ClC6H4 992 vinyl H Et H H H H 4-ClC6H4 993vinyl H Et H H H H 4-MeC6H4 994 vinyl H Et H H H H 4-t-BuC6H4 995 vinylH Et H H H H 1-Naph 996 vinyl H Et H H H H thiophene-2-yl 997 vinyl H EtH H H H pyridine-3-yl 998 vinyl H Et Me H H H 4-ClC6H4 999 vinyl H i-PrH H H H Ph 1000 vinyl H i-Pr H H H H 4-ClC6H4 1001 vinyl H i-Pr H H H H3,4-Cl2C6H3 1002 vinyl H i-Pr H H H H 2-MeC6H4 1003 vinyl H i-Pr H H H H4-MeC6H4 1004 vinyl H i-Pr H H H H 4-EtC6H4 1005 vinyl H i-Pr H H H H2-Naph 1006 vinyl H i-Pr H H H H thiophene-2-yl 1007 vinyl H i-Pr H H HH 5-methyl pyridine-3-yl 1008 vinyl H i-Pr Me H H H 4-MeC6H4 1009 vinylH s-Bu H H H H 4-ClC6H4 1010 vinyl H s-Bu H H H H 3,4-Cl2C6H3 1011 vinylH s-Bu H H H H 2-MeC6H4 1012 vinyl H s-Bu H H H H 4-MeC6H4 1013 vinyl Hs-Bu H H H H 4-t-BuC6H4 1014 vinyl H s-Bu H H H H 1-Naph 1015 vinyl Hs-Bu H H H H thiophene-2-yl 1016 vinyl H s-Bu H H H H isothiazole-5- yl1017 vinyl H s-Bu Me H H H 4-MeC6H4 1018 vinyl H i-Bu H H H H 4-ClC6H41019 vinyl H i-Bu H Ph H H 3,4-Cl2C6H3 1020 vinyl H i-Bu H H H H2-MeC6H4 1021 vinyl H i-Bu H H H H 4-MeC6H4 1022 vinyl H i-Bu H H H H4-t-BuC6H4 1023 vinyl H i-Bu H H H H 1-Naph 1024 vinyl H i-Bu H H H Hthiophene-2-yl 1025 vinyl H i-Bu H H H H isothiazole-5- yl 1026 vinyl Hi-Bu Me H H H 4-MeC6H4 1027 vinyl H t-Bu H H H H Ph 1028 vinyl H t-Bu HH H H 4-ClC6H4 1029 vinyl H t-Bu H H H H 3,4-Cl2C6H3 1030 vinyl H t-Bu HH H H 2-MeC6H4 1031 vinyl H t-Bu H H H H 4-MeC6H4 1032 vinyl H t-Bu H HH H 4-t-BuC6H4 1033 vinyl H t-Bu H H H H 1-Naph 1034 vinyl H t-Bu H H HH Thiophene- 2-yl 1035 vinyl H t-Bu H H H H Isothiazole- 5-yl 1036 vinylH t-Bu Me H H H 4-MeC6H4 1037 vinyl H Ph H H H H Ph 1038 vinyl H Ph H HH H 2-ClC6H4 1039 vinyl H Ph H H H H 4-ClC6H4 1040 vinyl H Ph H H H H4-MeC6H4 1041 vinyl H Ph H H H H 4-EtC6H4 1042 4-MeC6H4CH2 H Me H H H HPh 1043 4-MeC6H4CH2 H Me H H H H 2-BrC6H4 1044 4-MeC6H4CH2 H Me H H H H3-BrC6H4 1045 4-MeC6H4CH2 H Me H H H H 4-BrC6H4 1046 4-MeC6H4CH2 H Me HH H H 4-MeC6H4 1047 4-MeC6H4CH2 H i-Pr H H H H 2-ClC6H4 1048 4-MeC6H4CH2H i-Pr H H H H 3-ClC6H4 1049 4-MeC6H4CH2 H i-Pr H H H H 4-ClC6H4 10504-MeC6H4CH2 H i-Pr H H H H 4-MeC6H4 1051 4-MeC6H4CH2 H i-Pr H H H H4-EtC6H4 1052 4-MeC6H4CH2 H i-Bu H H H H Ph 1053 4-MeC6H4CH2 H i-Bu H HH H 2-FC6H4 1054 4-MeC6H4CH2 H i-Bu H H H H 3-FC6H4 1055 4-MeC6H4CH2 Hi-Bu H H H H 4-FC6H4 1056 4-MeC6H4CH2 H i-Bu H H H H 4-MeC6H4 10574-ClC6H4CH2 H Me H H H H Ph 1058 4-ClC6H4CH2 H Me H H H H 4-ClC6H4 10594-ClC6H4CH2 H Me H H H H 4-MeC6H4 1060 4-ClC6H4CH2 H Me H H H Hthiophene-2-yl 1061 4-ClC6H4CH2 H Me H H H H pyridine-3-yl 10624-ClC6H4CH2 H i-Pr H H H H Ph 1063 4-ClC6H4CH2 H i-Pr H H H H 4-ClC6H41064 4-ClC6H4CH2 H i-Pr H H H H 3,4-Cl2C6H3 1065 4-ClC6H4CH2 H i-Pr H HH H 2-MeC6H4 1066 4-ClC6H4CH2 H i-Pr H H H H 4-MeC6H4 1067 4-ClC6H4CH2 Hi-Bu H H H H Ph 1068 4-ClC6H4CH2 H i-Bu H H H H 2-MeC6H4 10694-ClC6H4CH2 H i-Bu H H H H 3-MeC6H4 1070 4-ClC6H4CH2 H i-Bu H H H H4-MeC6H4 1071 4-ClC6H4CH2 H i-Bu Me H H H 1-Naph 1072 PhCH(CH3) H Me H HH H Ph 1073 PhCH(CH3) H Me H H H H 4-ClC6H4 1074 PhCH(CH3) H Me H H H H4-MeC6H4 1075 PhCH(CH3) H Me H H H H thiophene-2-yl 1076 PhCH(CH3) H MeH H H H pyridine-4-yl 1077 PhCH(CH3) H i-Pr H H H H Ph 1078 PhCH(CH3) Hi-Pr H H H H 4-ClC6H4 1079 PhCH(CH3) H i-Pr H H H H 3,4-Cl2C6H3 1080PhCH(CH3) H i-Pr H H H H 2-MeC6H4 1081 PhCH(CH3) H i-Pr Me H H H4-MeC6H4 1082 PhCH(CH3) H i-Bu H H H H Ph 1083 PhCH(CH3) H i-Bu H H H H2-ClC6H4 1084 PhCH(CH3) H i-Bu H H H H 3-ClC6H4 1085 PhCH(CH3) H i-Bu HH H H 4-ClC6H4 1086 PhCH(CH3) H i-Bu H H H H 1-Naph 1087 PhCH(i-Pr) H MeH H H H Ph 1088 PhCH(i-Pr) H Me H H H H 4-ClC6H4 1089 PhCH(i-Pr) H Me HH H H 4-MeC6H4 1090 PhCH(i-Pr) H Me H H H H thiophene-2-yl 1091PhCH(i-Pr) H Me H H H H pyridine-2-yl 1092 PhCH(i-Pr) H i-Pr H H H H Ph1093 PhCH(i-Pr) H i-Pr H H H H 4-ClC6H4 1094 PhCH(i-Pr) H i-Pr H H H H3,4-Cl2C6H3 1095 PhCH(i-Pr) H i-Pr H H H H 2-MeC6H4 1096 PhCH(i-Pr) Hi-Pr H H H H 4-MeC6H4 1097 PhCH(i-Pr) H i-Bu H H H H Ph 1098 PhCH(i-Pr)H i-Bu H H H H 2-ClC6H4 1099 PhCH(i-Pr) H i-Bu H H H H 3-ClC6H4 1100PhCH(i-Pr) H i-Bu H H H H 4-ClC6H4 1101 PhCH(i-Pr) H i-Bu H H H H 1-Naph1102 PhC(CH3)2 H Me H H H H Ph 1103 PhC(CH3)2 H Me H H H H 4-ClC6H4 1104PhC(CH3)2 H Me H H H H 4-MeC6H4 1105 PhC(CH3)2 H Me H H H H furan-2-yl1106 PhC(CH3)2 H Me H H H H pyridine-4-yl 1107 PhC(CH3)2 H i-Pr H H H HPh 1108 PhC(CH3)2 H i-Pr H H H H 4-ClC6H4 1109 PhC(CH3)2 H i-Pr H H H H3,4-Cl2C6H3 1110 PhC(CH3)2 H i-Pr H H H H 2-MeC6H4 1111 PhC(CH3)2 H i-PrH H H H 4-MeC6H4 1112 PhC(CH3)2 H i-Bu H H H H Ph 1113 PhC(CH3)2 H i-BuH H H H 2-ClC6H4 1114 PbC(CH3)2 H i-Bu H H H H 3-ClC6H4 1115 PhC(CH3)2 Hi-Bu H H H H 4-ClC6H4 1116 PhC(CH3)2 H i-Bu H H H H 2-Naph 11172-furylmethyl H Me H H H H Ph 1118 2-furylmethyl H Me H H H H 4-ClC6H41119 2-furylmethyl H Me H H H H 4-MeC6H4 1120 2-furylmethyl H Me H H H Hthiophene-2-yl 1121 2-furylmethyl H Me H H H H pyridine-2-yl 11222-furylmethyl H i-Pr H H H H Ph 1123 2-furylmethyl H i-Pr H H H H4-ClC6H4 1124 2-furylmethyl H i-Pr H H H H 3,4-Cl2C6H3 11252-furylmethyl H i-Pr H H H H 2-MeC6H4 1126 2-furylmethyl H i-Pr H H H H4-MeC6H4 1127 2-furylmethyl H i-Bu H H H H Ph 1128 2-furylmethyl H i-BuH H H H 2-ClC6H4 1129 2-furylmethyl H i-Bu H H H H 3-ClC6H4 11302-furylmethyl H i-Bu H H H H 4-ClC6H4 1131 2-furylmethyl H i-Bu H H H H1-Naph 1132 3-furylmethyl H Me H H H H Ph 1133 3-furylmethyl H Me H H HH 4-ClC6H4 1134 3-furylmethyl H Me H H H H 4-MeC6H4 1135 3-furylmethyl HMe H H H H furan-2-yl 1136 3-furylmethyl H Me H H H H pyridine-4-yl 11373-furylmethyl H i-Pr H H H H Ph 1138 3-furylmethyl H i-Pr H H H H4-ClC6H4 1139 3-furylmethyl H i-Pr H H H H 3,4-Cl2C6H3 11403-furylmethyl H i-Pr H H H H 2-MeC6H4 1141 3-furylmethyl H i-Pr H H H H4-MeC6H4 1142 3-furylmethyl H i-Bu H H H H Ph 1143 3-furylmethyl H i-BuH H H H 2-ClC6H4 1144 3-furylmethyl H i-Bu H H H H 3-ClC6H4 11453-furylmethyl H i-Bu H H H H 4-ClC6H4 1146 3-furylmethyl H i-Bu H H H H2-Naph 1147 2-tetrahydrofurylmethyl H Me H H H H Ph 11482-tetrahydrofurylmethyl H Me H H H H 4-ClC6H4 11492-tetrahydrofurylmethyl H Me H H H H 4-MeC6H4 11502-tetrahydrofurylmethyl H Me H H H H thiophene-2-yl 11512-tetrahydrofurylmethyl H Me H H H H pyridine-2-yl 11522-tetrahydrofurylmethyl H i-Pr H H H H Ph 1153 2-tetrahydrofurylmethyl Hi-Pr H H H H 4-ClC6H4 1154 2-tetrahydrofurylmethyl H i-Pr H H H H3,4-Cl2C6H3 1155 2-tetrahydrofurylmethyl H i-Pr H H H H 2-MeC6H4 11562-tetrahydrofurylmethyl H i-Pr H H H H 4-MeC6H4 11572-tetrahydrofurylmethyl H i-Bu H H H H Ph 1158 2-tetrahydrofurylmethyl Hi-Bu H H H H 2-ClC6H4 1159 2-tetrahydrofurylmethyl H i-Bu H H H H3-ClC6H4 1160 2-tetrahydrofurylmethyl H i-Bu H H H H 4-ClC6H4 11612-tetrahydrofurylmethyl H i-Bu H H H H 1-Naph 1162 2-thienylmethyl H MeH H H H Ph 1163 2-thienylmethyl H Me H H H H 4-ClC6H4 11642-thienylmethyl H Me H H H H 4-MeC6H4 1165 2-thienylmethyl H Me H H H Hthiophene-2-yl 1166 2-thienylmethyl H Me H H H H pyridine-2-yl 11672-thienylmethyl H i-Pr H H H H Ph 1168 2-thienylmethyl H i-Pr H H H H4-ClC6H4 1169 2-thienylmethyl H i-Pr H H H H 3,4-Cl2C6H3 11702-thienylmethyl H i-Pr H H H H 2-MeC6H4 1171 2-thienylmethyl H i-Pr H HH H 4-MeC6H4 1172 2-thienylmethyl H i-Bu H H H H Ph 1173 2-thienylmethylH i-Bu H H H H 2-ClC6H4 1174 2-thienylmethyl H i-Bu H H H H 3-ClC6H41175 2-thienylmethyl H i-Bu H H H H 4-ClC6H4 1176 2-thienylmethyl H i-BuH H H H 1-Naph 1177 cyclopropylmethyl H Me H H H H Ph 1178cyclopropylmethyl H Me H H H H 4-ClC6H4 1179 cyclopropylmethyl H Me H HH H 4-MeC6H4 1180 cyclopropylmethyl H Me H H H H furan-2-yl 1181cyclopropylmethyl H Me H H H H pyridine-4-yl 1182 cyclopropylmethyl Hi-Pr H H H H Ph 1183 cyclopropylmethyl H i-Pr H H H H 4-ClC6H4 1184cyclopropylmethyl H i-Pr H H H H 3,4-Cl2C6H3 1185 cyclopropylmethyl Hi-Pr H H H H 2-MeC6H4 1186 cyclopropylmethyl H i-Pr H H H H 4-MeC6H41187 cyclopropylmethyl H i-Bu H H H H Ph 1188 cyclopropylmethyl H i-Bu HH H H 2-ClC6H4 1189 cyclopropylmethyl H i-Bu H H H H 3-ClC6H4 1190cyclopropylmethyl H i-Bu H H H H 4-ClC6H4 1191 cyclopropylmethyl H i-BuH H H H 2-Naph 1192 neopentyl H Me H H H H Ph 1193 neopentyl H Me H H HH 4-ClC6H4 1194 neopentyl H Me H H H H 4-MeC6H4 1195 neopentyl H Me H HH H thiophene-2-yl 1196 neopentyl H Me H H H H pyridine-2-yl 1197neopentyl H i-Pr H H H H Ph 1198 neopentyl H i-Pr H H H H 4-ClC6H4 1199neopentyl H i-Pr H H H H 3,4-Cl2C6H3 1200 neopentyl H i-Pr H H H H2-MeC6H4 1201 neopentyl H i-Pr H H H H 4-MeC6H4 1202 neopentyl H i-Bu HH H H Ph 1203 neopentyl H i-Bu H H H H 2-ClC6H4 1204 neopentyl H i-Bu HH H H 3-ClC6H4 1205 neopentyl H i-Bu H H H H 4-ClC6H4 1206 neopentyl Hi-Bu H H H H 1-Naph 1207 methallyl H Me H H H H Ph 1208 methallyl H Me HH H H 4-ClC6H4 1209 methallyl H Me H H H H 4-MeC6H4 1210 methallyl H MeH H H H furan-2-yl 1211 methallyl H Me H H H H pyridine-4-yl 1212methallyl H i-Pr H H H H Ph 1213 methallyl H i-Pr H H H H 4-ClC6H4 1214methallyl H i-Pr H H H H 3,4-Cl2C6H3 1215 methallyl H i-Pr H H H H2-MeC6H4 1216 methallyl H i-Pr H H H H 4-MeC6H4 1217 methallyl H i-Bu HH H H Ph 1218 methallyl H i-Bu H H H H 2-ClC6H4 1219 methallyl H i-Bu HH H H 3-ClC6H4 1220 methallyl H i-Bu H H H H 4-ClC6H4 1221 methallyl Hi-Bu H H H H 2-Naph 1222 1,2-dimethylpropyl H Me H H H H Ph 12231,2-dimethylpropyl H Me H H H H 4-ClC6H4 1224 1,2-dimethylpropyl H Me HH H H 4-MeC6H4 1225 1,2-dimethylpropyl H Me H H H H thiophene-2-yl 12261,2-dimethylpropyl H Me H H H H pyridine-2-yl 1227 1,2-dimethylpropyl Hi-Pr H H H H Ph 1228 1,2-dimethylpropyl H i-Pr H H H H 4-ClC6H4 12291,2-dimethylpropyl H i-Pr H H H H 3,4-Cl2C6H3 1230 1,2-dimethylpropyl Hi-Pr H H H H 2-MeC6H4 1231 1,2-dimethylpropyl H i-Pr H H H H 4-MeC6H41232 1,2-dimethylpropyl H i-Bu H H H H Ph 1233 1,2-dimethylpropyl H i-BuH H H H 2-ClC6H4 1234 1,2-dimethylpropyl H i-Bu H H H H 3-ClC6H4 12351,2-dimethylpropyl H i-Bu H H H H 4-ClC6H4 1236 1,2-dimethylpropyl Hi-Bu H H H H 1-Naph 1237 4-MeOC6H4CH2 H Me H H H H Ph 1238 4-MeOC6H4CH2H Me H H H H 4-ClC6H4 1239 4-MeOC6H4CH2 H Me H H H H 4-MeC6H4 12404-MeOC6H4CH2 H Me H H H H furan-2-yl 1241 4-MeOC6H4CH2 H Me H H H Hpyridine-4-yl 1242 4-MeOC6H4CH2 H i-Pr H H H H Ph 1243 4-MeOC6H4CH2 Hi-Pr H H H H 4-ClC6H4 1244 4-MeOC6H4CH2 H i-Pr H H H H 3,4-Cl2C6H3 12454-MeOC6H4CH2 H i-Pr H H H H 2-MeC6H4 1246 4-MeOC6H4CH2 H i-Pr H H H H4-MeC6H4 1247 4-MeOC6H4CH2 H i-Bu H H H H Ph 1248 4-MeOC6H4CH2 H i-Bu HH H H 2-ClC6H4 1249 4-MeOC6H4CH2 H i-Bu H H H H 3-ClC6H4 12504-MeOC6H4CH2 H i-Bu H H H H 4-ClC6H4 1251 4-MeOC6H4CH2 H i-Bu H H H H2-Naph 1252 2-(methylthio)ethyl H Me H H H H Ph 1253 2-(methylthio)ethylH Me H H H H 4-ClC6H4 1254 2-(methylthio)ethyl H Me H H H H 4-MeC6H41255 2-(methylthio)ethyl H Me H H H H thiophene-2-yl 12562-(methylthio)ethyl H Me H H H H pyridine-2-yl 1257 2-(methylthio)ethylH i-Pr H H H H Ph 1258 2-(methylthio)ethyl H i-Pr H H H H 4-ClC6H4 12592-(methylthio)ethyl H i-Pr H H H H 3,4-Cl2C6H3 1260 2-(methylthio)ethylH i-Pr H H H H 2-MeC6H4 1261 2-(methylthio)ethyl H i-Pr H H H H 4-MeC6H41262 2-(methylthio)ethyl H i-Bu H H H H Ph 1263 2-(methylthio)ethyl Hi-Bu H H H H 2-ClC6H4 1264 2-(methylthio)ethyl H i-Bu H H H H 3-ClC6H41265 2-(methylthio)ethyl H i-Bu H H H H 4-ClC6H4 12662-(methylthio)ethyl H i-Bu H H H H 1-Naph 1267 2-(methanesulfonyl)ethylH Me H H H H Ph 1268 2-(methanesulfonyl)ethyl H Me H H H H 4-ClC6H4 12692-(methanesulfonyl)ethyl H Me H H H H 4-MeC6H4 12702-(methanesulfonyl)ethyl H Me H H H H furan-2-yl 12712-(methanesulfonyl)ethyl H Me H H H H pyridine-4-yl 12722-(methanesulfonyl)ethyl H i-Pr H H H H Ph 1273 2-(methanesulfonyl)ethylH i-Pr H H H H 4-ClC6H4 1274 2-(methanesulfonyl)ethyl H i-Pr H H H H3,4-Cl2C6H3 1275 2-(methanesulfonyl)ethyl H i-Pr H H H H 2-MeC6H4 12762-(methanesulfonyl)ethyl H i-Pr H H H H 4-MeC6H4 12772-(methanesulfonyl)ethyl H i-Bu H H H H Ph 1278 2-(methanesulfonyl)ethylH i-Bu H H H H 2-ClC6H4 1279 2-(methanesulfonyl)ethyl H i-Bu H H H H3-ClC6H4 1280 2-(methanesulfonyl)ethyl H i-Bu H H H H 4-ClC6H4 12812-(methanesulfonyl)ethyl H i-Bu H H H H 2-Naph 1282 2-thienyl H Me H H HH Ph 1283 2-thienyl H Me H H H H 4-ClC6H4 1284 2-thienyl H Me H H H H4-MeC6H4 1285 2-thienyl H Me H H H H thiophene-2-yl 1286 2-thienyl H MeH H H H pyridine-2-yl 1287 2-thienyl H i-Pr H H H H Ph 1288 2-thienyl Hi-Pr H H H H 4-ClC6H4 1289 2-thienyl H i-Pr H H H H 3,4-Cl2C6H3 12902-thienyl H i-Pr H H H H 2-MeC6H4 1291 2-thienyl H i-Pr H H H H 4-MeC6H41292 2-thienyl H i-Bu H H H H Ph 1293 2-thienyl H i-Bu H H H H 2-ClC6H41294 2-thienyl H i-Bu H H H H 3-ClC6H4 1295 2-thienyl H i-Bu H H H H4-ClC6H4 1296 2-thienyl H i-Bu H H H H 1-Naph

TABLE 2 Analytical data Comp. No. Analytical data 4 ¹H NMR(CDCl₃, ppm):1.15(3H, d, J = 6.1 Hz), 3.46–3.61(2H, m), 3.63(3H, s), 3.66–3.72(1H,m), 4.86(1H, d, J = 8.5 Hz), 6.86(1H, br-s), 7.41(2H, d, J = 8.1 Hz),7.74(2H, d, J = 8.1 Hz). 26 ¹H NMR(CDCl₃, ppm): 1.00(6H, t, J = 8.1 Hz),1.85–1.89(1H, m), 3.46–3.61(2H, m), 3.63(3H, s), 3.66–3.72(1H, m),4.86(1H, d, J = 8.5 Hz), 6.86(1H, br-s), 7.39–7.49 (3H, m), 7.79(2H, d,J = 7.1 Hz). 30 ¹H NMR(CDCl₃, ppm): 1.00(6H, t, J = 8.1 Hz),1.85–1.89(1H, m), 2.39(3H, s), 3.46–3.61(2H, m), 3.63(3H, s),3.66–3.72(1H, m), 4.86(1H, d, J = 8.5 Hz), 6.86(1H, br-s), 7.23(2H, d, J= 8.1 Hz), 7.68(2H, d, J = 8.1 Hz). 66 ¹H NMR(CDCl₃, ppm): 3.46–3.61(2H,m), 3.63(3H, s), 3.66–3.72(1H, m), 4.86(1H, d, J = 8.5 Hz), 6.86(1H,br-s), 7.23–7.41(5H, m), 7.39–7.49(3H, m), 7.79 1(2H, d, J = 7.1 Hz).215 ¹H NMR(CDCl₃, ppm): 1.14(3H, d, J = 6.1 Hz), 1.22(3H, d, J = 6.8Hz), 1.24(3H, d, J = 6.8 Hz), 2.39(3H, s), 3.48–3.53(2H, m),3.96–3.99(1H, m), 4.79(1H, br-s), 4.84–4.91(1H, m), 7.23(2H, d, J = 8.1Hz), 7.70(2H, d, J = 8.1 Hz). 216 ¹H NMR(CDCl₃, ppm): 1.14(3H, d, J =6.1 Hz), 1.22(3H, d, J = 6.8 Hz), 1.24(3H, d, J = 6.8 Hz), 1.32(9H, s),3.48–3.53(2H, m), 3.96–3.99(1H, m), 4.79(1H, br-s), 4.84–4.91(1H, m),7.23(2H, d, J = 8.1 Hz), 7.70(2H, d, J = 8.1 Hz). 236 ¹H NMR(CDCl₃,ppm): 1.01(6H, t, J = 7.1 Hz), 1.09(3H, d, J = 6.1 Hz), 1.22(3H, d, J =6.1 Hz), 1.85–1.89(1H, m), 3.48–3.61(2H, m), 3.68–3.74(1H, m), 4.12(1H,d, J = 7.3 Hz), 4.73–4.89(1H, m), 7.06(1H, br-s), 7.40–7.50(3H, m),7.80(2H, d, J = 7.1 Hz). 237 ¹H NMR(CDCl₃, ppm): 1.00(3H, d, J = 6.8Hz), 1.01(3H, d, J = 6.8 Hz), 1.11(3H, d, J = 6.1 Hz), 1.23(3H, d, J =6.1 Hz), 1.85–1.90(1H, m), 3.50–3.54(2H, m), 3.67–3.73 (1H, m), 4.73(1H,d, J = 8.8 Hz), 4.83–4.90(1H, m), 7.21(1H, br-s), 7.40(2H, d, J = 8.5Hz), 7.75(2H, d, J = 8.5 Hz). 238 ¹H NMR(CDCl₃, ppm): 1.01(6H, t, J =6.8 Hz), 1.14(3H, d, J = 6.3 Hz), 1.24(3H, d, J = 6.3 Hz), 1.85–1.90(1H,m), 3.50–3.53(2H, m), 3.67–3.72(1H, m), 4.75(1H, d, J = 8.3 Hz),4.86–4.92(1H, m), 7.35(1H, br-s), 7.50(1H, d, J = 8.3 Hz), 7.62(1H, d, J= 8.3 Hz), 7.94(1H, s). 239 ¹H NMR(CDCl₃, ppm): 0.98(3H, d, J = 6.8 Hz),1.00(3H, d, J = 6.8 Hz), 1.17(3H, d, J = 6.3 Hz), 1.21(3H, d, J = 6.3Hz), 1.83–1.88(1H, m), 2.44(3H, s), 3.41–3.47(1H, m), 3.56–3.70(2H, m),4.77(1H, d, J = 8.5 Hz), 4.82–4.88(1H, m), 6.29(1H br-s), 7.16–7.35(4H,m). 240 ¹H NMR(CDCl₃, ppm): 0.99(3H, d, J = 7.3 Hz), 1.01(3H, d, J = 7.3Hz), 1.10(3H, d, J = 6.1 Hz), 1.21(3H, d, J = 6.1 Hz), 1.84–1.88(1H, m),2.38(3H, s), 3.47–3.60(2H, m), 3.67–3.73(1H, m), 4.75(1H, d, J = 8.5Hz), 4.83–4.89(1H, m), 6.99(1H, br-s), 7.22 (2H, d, J = 8.1 Hz),7.69(2H, d, J = 8.1 Hz). 241 ¹H NMR(CDCl₃, ppm): 1.00(6H, t, J = 7.3Hz), 1.09(3H, d, J = 6.2 Hz), 1.21–1.26(6H, m), 1.82–1.90(1H, m),2.68(2H, q, J = 7.6 Hz), 3.46–3.62(2H, m), 3.68–3.76(1H, m), 4.74(1H, d,J = 8.8 Hz), 4.87–4.90(1H, m), 6.99(1H, d, J = 8.1 Hz), 7.24(2H, d, J =8.5 Hz), 7.72(2H, d, J = 8.5 Hz). 242 ¹H NMR(CDCl₃, ppm): 1.03(6H, t, J= 6.8 Hz), 1.09(3H, d, J = 6.1 Hz), 1.22(3H, d, J = 6.1 Hz),1.87–1.92(1H, m), 3.54–3.67(2H, m), 3.74–3.78(1H, m), 4.77(1H, d, J =8.5 Hz), 4.86–4.92(1H, m), 7.23(1H, br-s), 7.51–7.58(2H, m),7.86–7.94(4H, m), 8.34(1H, s). 243 ¹H NMR(CDCl₃, ppm): 0.97–1.00(6H, m),1.11(3H, d, J = 6.3 Hz), 1.22(3H, d, J = 6.3 Hz), 1.80–1.90(1H, m),2.50(3H, s), 3.44–3.57(2H, m), 3.66–3.73(1H, m), 4.76(1H, d, J = 8.5Hz), 4.87–4.90(1H, m), 6.71(1H, d, J = 3.7 Hz), 6.87(1H, br-s), 7.30(1H,d, J = 3.7 Hz) 245 ¹H NMR(CDCl₃, ppm): 0.93(3H, d, J = 7.1 Hz), 0.95(3H,d, J = 7.1 Hz), 1.15(3H, s), 1.23(6H, d, J = 6.3 Hz), 2.35–2.40(4H, m),3.60(1H, dd, J = 5.1 Hz, 14.2 Hz), 3.82 (1H, dd, J = 5.9 Hz, 14.2 Hz),4.72(1H, br-s), 4.87–4.93(1H, m), 7.24(2H, d, J = 8.1 Hz), 7.76(2H, d, J= 8.1 Hz). 246 ¹H NMR(CDCl₃, ppm): 1.00–1.03(6H, m), 1.17(3H, d, J = 6.6Hz), 1.26(6H, d, J = 6.3 Hz), 1.65–1.69(1H, m), 2.39(3H, s),3.51–3.56(1H, m), 4.33–4.37(1H, m), 4.56(1H, d, J = 8.0 Hz),4.92–5.00(1H, m), 7.23(2H, d, J = 8.3 Hz), 7.30(1H, br-s), 7.72(2H, d, J= 8.3 Hz). 247 ¹H NMR(CDCl₃, ppm): 0.99–1.03(6H, m), 1.18(3H, d, J = 6.6Hz), 1.26(6H, d, J = 6.3 Hz), 1.62–1.67(1H, m), 3.50–3.54(1H, m),4.33–4.35(1H, m), 4.53(1H, d, J = 8.0 Hz), 4.91–4.98(1H, m), 7.22(2H, d,J = 8.3 Hz), 7.31(1H, br-s), 7.74(2H, d, J = 8.3 Hz). 279 ¹H NMR(CDCl₃,ppm): 1.15–1.26(6H, m), 2.40(3H, s), 3.25–3.30(1H, m), 3.42–3.50 (1H,m), 4.82–4.90(1H, m), 4.92–4.98(1H, m), 5.60(1H, d, J = 7.1 Hz),6.84(1H, br-s), 7.22–7.40(7H, m), 7.67(2H, d, J = 7.8 Hz). 284 ¹HNMR(CDCl₃, ppm): 1.13–1.19(6H, m), 2.40(3H, m), 3.70–3.80(2H, m),4.82–4.92 (2H, m), 5.80(1H, d, J = 7.1 Hz), 6.65(1H, br-s),7.21–7.29(4H, m), 7.34(2H, d, J = 8.1 Hz), 7.65(2H, d, J = 8.1 Hz). M⁺:375. 289 ¹H NMR(CDCl₃, ppm): 1.12(3H, d, J = 6.1 Hz), 1.18(3H, d, J =6.1 Hz), 2.38(3H, s), 2.80–2.86(1H, m), 2.92–2.98(1H, m), 3.49–3.56(2H,m), 4.07–4.15(1H, m), 4.81–4.88(1H, m), 4.95(1H, d, J = 7.3 Hz),6.88(1H, br-s), 7.20–7.27(5H, m), 7.31 (2H, d, J = 8.1 Hz), 7.65(2H, d,J = 8.1 Hz). 290 ¹H NMR(CDCl₃, ppm): 1.12(3H, d, J = 6.1 Hz), 1.18(3H,d, J = 6.1 Hz), 1.20–1.25(3H, m), 2.67(2H, q, J = 7.6 Hz), 2.80–2.86(1H,m), 2.92–2.98(1H, m), 3.49–3.56(2H, m), 4.07–4.15(1H, m), 4.81–4.88(1H,m), 4.95(1H, d, J = 7.3 Hz), 6.88(1H, br-s), 7.20–7.27(5H, m), 7.31(2H,d, J = 8.1 Hz), 7.65(2H, d, J = 8.1 Hz). 384 ¹H NMR(CDCl₃, ppm):0.85(3H, d, J = 6.6 Hz), 0.86(3H, d, J = 6.6 Hz), 1.01(6H, t, J = 6.6Hz), 1.79–1.89(1H, m), 3.47–3.71(3H, m), 3.80(2H, d, J = 6.8 Hz),4.82(1H, d, J = 8.3 Hz), 6.92(br-s), 7.41(2H, d, J = 8.3 Hz), 7.76(2H,d, J = 8.3 Hz). 387 ¹H NMR(CDCl₃, ppm): 0.84(3H, d, J = 6.8 Hz),0.85(3H, d, J = 6.8 Hz), 1.06(6H, d, J = 6.8 Hz), 1.63–1.89(2H, m),2.39(3H, s), 3.46–3.74(3H, m), 3.80(2H, d, J = 6.6 Hz), 4.82(1H, d, J =8.8 Hz), 6.92(1H, br-s), 7.22(2H, d, J = 7.8 Hz), 7.68(2H, d, J = 7.8Hz). 464 ¹H NMR(CDCl₃, ppm): 1.00(6H, t, J = 6.8 Hz), 1.39(9H, s),1.82–1.87(1H, m), 2.38 (3H, s), 3.46–3.53(2H, m), 3.65–3.69(1H, m),4.65(1H, d, J = 8.5 Hz), 7.04(1H, br-s), 7.21(2H, d, J = 8.1 Hz),7.70(2H, d, J = 8.1 Hz). 469 ¹H NMR(CDCl₃, ppm): 0.92(3H, d, J = 6.8Hz), 0.94(3H, d, J = 6.8 Hz), 1.13(3H, s), 2.37–2.41(4H, m), 3.57(1H,dd, J = 5.6 Hz), 13.7 Hz), 3.81(1H, dd, J = 5.6 Hz), 13.7 Hz), 4.62(1H,br-s), 7.24(2H, d, J = 8.1 Hz), 7.77(2H, d, J = 8.1 Hz), 8.17(1H, br-s).470 ¹H NMR(CDCl₃, ppm): 1.00–1.03(6H, m), 1.17(3H, d, J = 6.6 Hz),1.49(9H, s), 1.58–1.67(1H, m), 3.47–3.53(1H, m), 4.33–4.35(1H, m),4.51(1H, d,, J = 8.0 Hz), 7.23(2H, d, J = 8.3 Hz), 7.38(1H, br-s),7.73(2H, d, J = 8.3 Hz). 471 ¹H NMR(CDCl₃, ppm): 1.00–1.03(6H, m),1.16(3H, d, J = 6.6 Hz), 1.49(9H, s), 1.59–1.68(1H, m), 2.38(3H, s),3.46–3.52(1H, m), 4.33–4.35(1H, m), 4.51(1H, d, J = 8.0 Hz), 7.21(2H, d,J = 8.3 Hz), 7.36(1H, br-s), 7.72(2H, d, J = 8.3 Hz). 504 ¹H NMR(CDCl₃,ppm): 1.40(9H, s), 2.40(3H, s), 3.25–3.30(1H, m), 3.42–3.50(1H, m),4.82–4.90(1H, m), 5.60(1H, d, J = 7.1 Hz), 6.84(1H, br-s), 7.22–7.40(7H,m), 7.67(2H, d, J = 7.8 Hz). 526 ¹H NMR(CDCl₃, ppm): 1.05(3H, d, J = 6.8Hz), 1.07(3H, d, J = 6.8 Hz), 1.91–1.96 (1H, m), 2.40(3H, s),3.47–3.50(1H, m), 3.74–3.78(2H, m), 5.26(1H, d, J = 7.6 Hz), 6.76(1H,br-s), 7.15–7.31(5H, m), 7.40–7.50(3H, m), 7.80(2H, d, J = 7.3 Hz). 530¹H NMR(CDCl₃, ppm): 1.05(3H, d, J = 6.8 Hz), 1.07(3H, d, J = 6.8 Hz),1.91–1.96 (1H, m), 2.40(3H, s), 3.47–3.50(1H, m), 3.74–3.78(2H, m),5.26(1H, d, J = 7.6 Hz), 6.76(1H, br-s), 6.95(2H, d, J = 8.3 Hz),7.15–7.31(5H, m), 7.68(2H, d, J = 8.3 Hz). 596 ¹H NMR(CDCl₃, ppm):0.99(3H, d, J = 6.8 Hz), 1.01(3H, d, J = 6.8 Hz), 1.85–1.90 (1H, m),2.39(3H, s), 3.48–3.62(2H, m), 3.69–3.74(1H, m), 4.94(1H, d, J = 8.8Hz), 5.06(2H, d, J = 7.1 Hz), 6.86(1H, br-s), 7.20–7.30(7H, m),7.41–7.51(3H, m), 7.79(2H, d, J = 7.1 Hz). 600 ¹H NMR(CDCl₃, ppm):0.99(3H, d, J = 6.8 Hz), 1.01(3H, d, J = 6.8 Hz), 1.85–1.90 (1H, m),2.39(3H, s), 3.48–3.62(2H, m), 3.69–3.74(1H, m), 4.94(1H, d, J = 8.8Hz), 5.06(2H, d, J = 7.1 Hz), 6.86(1H, br-s), 7.20–7.30(7H, m), 7.65(2H,d, J = 8.1 Hz). 636 ¹H NMR(CDCl₃, ppm): 3.48–3.62(2H, m), 3.69–3.74(1H,m), 4.94(1H, d, J = 8.8 Hz), 5.06(2H, d, J = 7.1 Hz), 6.86(1H, br-s),7.20–7.40(14H, m), 7.82(2H, d, J = 7.1 Hz). 674 ¹H NMR(CDCl₃, ppm):1.10(3H, d, J = 6.8 Hz), 1.12(3H, d, J = 6.8 Hz), 1.94–2.01 (1H, m),3.50–3.55(1H, m), 3.80–3.84(2H, m), 5.31(1H, d, J = 8.5 Hz), 6.78(1H,br-s), 7.10(1H, d, J = 8.8 Hz), 7.21(2H, d, J = 7.8 Hz), 7.37(1H, s),7.41–7.56(2H, m), 7.60–7.90(5H, m). 677 ¹H NMR(CDCl₃, ppm): 1.09(3H, d,J = 6.8 Hz), 1.10(3H, d, J = 6.8 Hz), 1.94–1.99 (1H, m), 2.40(3H, s),3.47–3.51(1H, m), 3.80–3.84(2H, m), 5.30(1H, d, J = 8.5 Hz), 6.77(1H,br-s), 7.10(1H, d, J = 8.8 Hz), 7.21(2H, d, J = 7.8 Hz), 7.34(1H, s),7.41–7.54(2H, m), 7.63–7.93(5H, m). 739 ¹H NMR(CDCl₃, ppm): 1.00(6H, t,J = 7.3 Hz), 1.85–1.90(1H, m), 3.46–3.74(3H, m), 4.52(2H, d, J = 5.6Hz), 4.93(1H, d, J = 8.3 Hz), 5.14(1H, d, J = 10.5 Hz), 5.25 (1H, d, J =17.1 Hz), 4.79–5.88(1H, m), 6.88(1H, br-s), 7.39(2H, d, J = 8.1 Hz),7.73(2H, d, J = 8.1 Hz). 742 ¹H NMR(CDCl₃, ppm): 1.00(6H, t, J = 7.3Hz), 1.85–1.90(1H, m), 2.39(3H, s), 3.46–3.74(3H, m), 4.52(2H, d, J =5.6 Hz), 4.93(1H, d, J = 8.3 Hz), 5.14(1H, d, J = 10.5 Hz), 5.25(1H, d,J = 17.1 Hz), 4.79–5.88(1H, m), 6.88(1H, br-s), 7.22(2H, d, J = 8.1 Hz),7.68(2H, d, J = 8.1 Hz). 804 ¹H NMR(CDCl₃, ppm): 1.00(6H, t, J = 7.8Hz), 1.86–1.91(1H, m), 2.36(1H, s), 3.47–3.74(3H, m), 4.63(2H, s),5.01(1H, d, J = 9.0 Hz), 6.79(1H, br-s), 7.38(2H, d, J = 8.1 Hz),7.73(2H, d, J = 8.1 Hz). 807 ¹H NMR(CDCl₃, ppm): 1.00(6H, t, J = 7.8Hz), 1.86–1.91(1H, m), 2.36(1H, s), 2.39 (3H, s), 3.47–3.74(3H, m),4.63(2H, s), 5.01(1H, d, J = 9.0 Hz), 6.79(1H, br-s), 7.22 (2H, d, J =8.1 Hz), 7.68(2H, d, J = 8.1 Hz). 1049 ¹H NMR(CDCl₃, ppm): 0.98(3H, d, J= 7.1 Hz), 1.00(3H, d, J = 7.1 Hz), 1.84–1.89(1H, m), 2.31(3H, s),3.49–3.57(2H, m), 3.69–3.75(1H, m), 4.92(1H, d, J = 9.0 Hz), 5.00 (1H,d, J = 12.2 Hz), 5.05(1H, d, J = 12.2 Hz), 7.00(1H, br-s), 7.07(2H, d, J= 8.1 Hz), 7.16(2H, d, J = 7.8 Hz), 7.24(2H, d, J = 8.1 Hz), 7.67(2H, d,J = 7.8 Hz). 1050 ¹H NMR(CDCl₃, ppm): 0.98(3H, d, J = 7.1 Hz), 1.00(3H,d, J = 7.1 Hz), 1.84–1.89(1H, m), 2.31(3H, s), 2.40(3H, s),3.49–3.57(2H, m), 3.69–3.75(1H, m), 4.92(1H, d, J = 9.0 Hz), 5.00(1H, d,J = 12.2 Hz), 5.05(1H, d, J = 12.2 Hz), 7.00(1H, br-s), 7.07 (2H, d, J =8.1 Hz), 7.16(2H, d, J = 7.8 Hz), 7.22(2H, d, J = 8.1 Hz), 7.65(2H, d, J= 7.8 Hz). 1063 ¹H NMR(CDCl₃, ppm): 1.00(6H, t, J = 7.1 Hz),1.83–1.90(1H, m), 3.43–3.47(1H, m), 3.62–3.73(2H, m), 4.94(1H, d, J =12.4 Hz), 4.95(1H, d, J = 9.0 Hz), 5.06(1H, d, J = 12.4 Hz), 6.73(1H,br-s), 7.17–7.22(6H, m), 7.59(2H, d, J = 8.1 Hz). 1066 ¹H NMR(CDCl₃,ppm): 1.00(6H, t, J = 7.1 Hz), 1.83–1.90(1H, m), 2.41(3H, s),3.43–3.47(1H, m), 3.62–3.73(2H, m), 4.94(1H, d, J = 12.4 Hz), 4.95(1H,d, J = 9.0 Hz), 5.06(1H, d, J = 12.4 Hz), 6.73(1H, br-s), 7.17–7.22(6H,m), 7.61(2H, d, J = 8.1 Hz). 1078 ¹H NMR(CDCl₃, ppm): 0.95–1.02(6H, m),1.39(3 × 1/2H, d, J = 6.6 Hz), 1.51(3H × 1/2, d, J = 6.6 Hz),1.80–1.88(1H, m), 3.40–3.64(3H, m), 4.90(1H × 1/2, d, J = 8.5 Hz),4.96(1H × 1/2, d, J = 9.0 Hz), 5.70–5.77(1H, m), 6.71(1H × 1/2, br-s),6.78(1H × 1/2, br-s), 7.09–7.36(6H, m), 7.45(2H × 1/2, d, J = 8.3 Hz),7.69(2H × 1/2, d, J = 8.3 Hz). 1081 ¹H NMR(CDCl₃, ppm): 0.95–1.02(6H,m), 1.39(3H × 1/2, d, J = 6.6 Hz), 1.51(3H × 1/2, d, J = 6.6 Hz),1.80–1.88(1H, m), 2.37(3H × 1/2, s), 2.40(3H × 1/2, s), 3.40–3.64(3H,m), 4.90(1H × 1/2, d, J = 8.5 Hz), 4.96(1H × 1/2, d, J = 9.0 Hz),5.70–5.77(1H, m), 6.71(1H × 1/2, br-s), 6.78(1H × 1/2, br-s),7.09–7.36(6H, m), 7.47(2H × 1/2, d, J = 8.3 Hz), 7.71(2H × 1/2, d, J =8.3 Hz). 1123 ¹H NMR(CDCl₃, ppm): 0.99(3H, d, J = 6.8 Hz), 1.02(3H, d, J= 6.8 Hz), 1.85–1.89(1H, m), 3.51–3.54(2H, m), 3.72–3.76(1H, m),4.90(1H, d, J = 9.0 Hz), 5.02(2H, d, J = 4.9 Hz), 6.29(1H, d, J = 3.2Hz), 6.31(1H, d, J = 3.2 Hz), 6.85(1H, br-s), 7.20(2H, d, J = 8.1 Hz),7.33(1H, s), 7.66(2H, d, J = 8.1 Hz). 1126 ¹H NMR(CDCl₃, ppm): 0.98(3H,d, J = 6.8 Hz), 1.00(3H, d, J = 6.8 Hz), 1.85–1.89(1H, m), 2.40(3H, s),3.51–3.54(2H, m), 3.70–3.76(1H, m), 4.90(1H, d, J = 9.0 Hz), 5.02 (2H,d, J = 4.9 Hz), 6.29(1H, d, J = 3.2 Hz), 6.33(1H, d, J = 3.2 Hz),6.87(1H, br-s), 7.23(2H, d, J = 8.1 Hz), 7.33(1H, s), 7.68(2H, d, J =8.1 Hz). 1138 ¹H NMR(CDCl₃, ppm): 0.98(3H, d, J = 6.8 Hz), 1.00(3H, d, J= 6.8 Hz), 1.84–1.89(1H, m), 3.48–3.61(2H, m), 3.68–3.73(1H, m),4.88(1H, d, J = 6.8 Hz), 4.92(2H, s), 6.34 (1H, s), 6.80(1H, br-s),7.20(2H, d, J = 7.8 Hz), 7.29(1H, d, J = 2.0 Hz), 7.41(1H, d, J = 2.0Hz), 7.63(2H, d, J = 7.8 Hz). 1141 ¹H NMR(CDCl₃, ppm): 0.98(3H, d, J =6.8 Hz), 1.00(3H, d, J = 6.8 Hz), 1.84–1.89(1H, m), 2.40(3H, s),3.48–3.61(2H, m), 3.68–3.73(1H, m), 4.88(1H, d, J = 6.8 Hz), 4.92 (2H,s), 6.33(1H, s), 6.83(1H, br-s), 7.22(2H, d, J = 7.8 Hz), 7.31(1H, d, J= 2.0 Hz), 7.39(1H, d, J = 2.0 Hz), 7.65(2H, d, J = 7.8 Hz). 1153 ¹HNMR(CDCl₃, ppm): 1.00(3H, d, J = 6.8 Hz), 1.01(3H, d, J = 6.8 Hz),1.49–1.56(1H, m), 1.81–1.95(4H, m), 3.51–3.54(2H, m), 3.65–4.16(6H, m),4.95(1H, d, J = 8.5 Hz), 6.91(1H, br-s), 7.24(2H, d, J = 8.1 Hz),7.70(2H, d, J = 8.1 Hz). 1156 ¹H NMR(CDCl₃, ppm): 0.99(3H, d, J = 6.8Hz), 1.01(3H, d, J = 6.8 Hz), 1.49–1.56(1H, m), 1.81–1.95(4H, m),2.39(3H, s), 3.51–3.55(2H, m), 3.67–4.16(6H, m), 4.95(1H, d, J = 8.5Hz), 6.93(1H, br-s), 7.22(2H, d, J = 8.1 Hz), 7.68 (2H, d, J = 8.1 Hz).1168 ¹H NMR(CDCl₃, ppm): 0.98(3H, d, J = 6.8 Hz), 1.00(3H, d, J = 6.8Hz), 1.85–1.89(1H, m), 3.51–3.56(2H, m), 3.70–3.75(1H, m), 4.91(1H, d, J= 8.8 Hz), 5.19(1H, d, J = 12.7 Hz), 5.22(1H, d, J = 12.7 Hz), 6.83(1H,br-s), 6.91(1H, dd, J = 1.7 Hz, 3.4 Hz), 7.01 (1H, dd, J = 1.7 Hz, 3.4Hz), 7.21–7.25(3H, m), 7.68(2H, d, J = 8.1 Hz). 1171 ¹H NMR(CDCl₃, ppm):0.98(3H, d, J = 6.8 Hz), 1.00(3H, d, J = 6.8 Hz), 1.85–1.89 (1H, m),2.40(3H, s), 3.51–3.56(2H, m), 3.70–3.75(1H, m), 4.92(1H, d, J = 8.8Hz), 5.19(1H, d, J = 12.7 Hz), 5.22(1H, d, J = 12.7 Hz), 6.85(1H, br-s),6.91(1H, dd, J = 1.7 Hz, 3.4 Hz), 7.01(1H, dd, J = 1.7 Hz, 3.4 Hz),7.21–7.24(3H, m), 7.66 (2H, d, J = 8.1 Hz). 1183 ¹H NMR(CDCl₃, ppm):0.19–0.23(2H, m), 0.45–0.50(2H, m), 1.01(6H, t, J = 7.1 Hz),1.86–1.93(1H, m), 3.48–3.64(2H, m), 3.67–3.75(1H, m), 3.85(2H, d, J =7.3 Hz), 4.87(1H, d, J = 9.0 Hz), 6.96(1H, br-s), 7.23(2H, d, J = 8.5Hz), 7.69(2H, d, J = 8.5 Hz). 1186 ¹H NMR(CDCl₃, ppm): 0.19–0.23(2H, m),0.45–0.49(2H, m), 1.01(6H, t, J = 7.1 Hz), 1.86–1.93(1H, m), 2.38(3H,s), 3.48–3.62(2H, m), 3.67–3.75(1H, m), 3.84 (2H, d, J = 7.3 Hz),4.86(1H, d, J = 9.0 Hz), 6.96(1H, br-s), 7.21(2H, d, J = 8.5 Hz),7.68(2H, d, J = 8.5 Hz). 1198 ¹H NMR(CDCl₃, ppm): 0.86(9H, s), 1.03(6H,t, J = 5.6 Hz), 1.86–1.90(1H, m), 3.48–3.68(2H, m), 3.70–3.75(3H, m),4.84(1H, d, J = 8.5 Hz), 6.92(1H, d, J = 6.6 Hz), 7.20(2H, d, J = 8.1Hz), 7.65(2H, d, J = 8.1 Hz). 1201 ¹H NMR(CDCl₃, ppm): 0.86(9H, s),1.01(6H, t, J = 5.6 Hz), 1.86–1.91(1H, m), 2.39(3H, s), 3.48–3.68(2H,m), 3.70–3.76(3H, m), 4.84(1H, d, J = 8.5 Hz), 6.94 (1H, d, J = 6.6 Hz),7.22(2H, d, J = 8.1 Hz), 7.67(2H, d, J = 8.1 Hz). 1213 ¹H NMR(CDCl₃,ppm): 1.03(6H, t, J = 7.1 Hz), 1.68(3H, s), 1.84–1.90(1H, m),3.46–3.75(3H, m), 4.45(2H, s), 4.83(1H, s), 4.90–4.95(2H, m), 6.87(1H,br-s), 7.22(2H, d, J = 8.1 Hz), 7.68(2H, d, J = 8.1 Hz). 1216 ¹HNMR(CDCl₃, ppm): 1.01(6H, t, J = 7.1 Hz), 1.67(3H, s), 1.84–1.90(1H, m),2.39(3H, s), 3.46–3.75(3H, m), 4.44(2H, s), 4.83(1H, s), 4.90–4.94(2H,m), 6.87 (1H, br-s), 7.21(2H, d, J = 8.1 Hz), 7.67(2H, d, J = 8.1 Hz).1228 ¹H NMR(CDCl₃, ppm): 0.75(3H, d, J = 6.6 Hz), 0.90(3H, d, J = 6.6Hz), 1.01(6H + 3H × 1/2, t, J = 6.6 Hz), 1.13(3H × 1/2, d, J = 6.6 Hz),1.82–1.91(1H, m), 3.45–3.65 (2H, m), 3.69–3.77(1H, m), 4.56–4.61(1H, m),4.75(1H, t, J = 8.1 Hz), 6.94(1H, d, J = 9.0 Hz), 7.20–7.24(2H, m),7.66(2H, t, J = 7.6 Hz). 1231 ¹H NMR(CDCl₃, ppm): 0.75(3H, d, J = 6.6Hz), 0.89(3H, d, J = 6.6 Hz), 1.01(6H + 3H × 1/2, t, J = 6.6 Hz),1.14(3H × 1/2, d, J = 6.6 Hz), 1.82–1.91(1H, m), 2.38(3H, s),3.45–3.65(2H, m), 3.69–3.76(1H, m), 4.56–4.62(1H, m), 4.75(1H, t, J =8.1 Hz), 6.95(1H, d, J = 9.0 Hz), 7.20–7.23(2H, m), 7.68(2H, t, J = 7.6Hz). 1258 ¹H NMR(CDCl₃, ppm): 1.00(6H, t, J = 7.6 Hz), 1.86–1.92(1H, m),2.05(3H, s), 2.62(2H, t, J = 6.8 Hz), 3.47–3.73(3H, m), 4.15–4.24(2H,m), 4.89(1H, d, J = 8.5 Hz), 6.84(1H, br-s), 7.22(2H, d, J = 8.1 Hz),7.67(2H, d, J = 8.1 Hz). 1261 ¹H NMR(CDCl₃, ppm): 1.00(6H, t, J = 7.6Hz), 1.86–1.91(1H, m), 2.07(3H, s), 2.39(3H, s), 2.62(2H, t, J = 6.8Hz), 3.47–3.72(3H, m), 4.15–4.23(2H, m), 4.89 (1H, d, J = 8.5 Hz),6.81(1H, br-s), 7.23(2H, d, J = 8.1 Hz), 7.68(2H, d, J = 8.1 Hz). 1273¹H NMR(CDCl₃, ppm): 0.98(3H, d, J = 6.8 Hz), 1.02(3H, d, J = 6.8 Hz),1.83–1.90 (1H, m), 2.40(3H, s), 3.13–3.18(2H, m), 3.41–3.45(1H, m),3.66–3.70(2H, m), 4.34–4.40(1H, m), 4.49–4.54(1H, m), 5.20(1H, d, J =8.1 Hz), 6.64(1H, br-s), 7.26 (2H, d, J = 7.8 Hz), 7.65(2H, d, J = 7.8Hz). 1276 ¹H NMR(CDCl₃, ppm): 0.99(3H, d, J = 6.8 Hz), 1.01(3H, d, J =6.8 Hz), 1.83–1.90 (1H, m), 2.40(3H, s), 2.81(3H, s), 3.13–3.16(2H, m),3.41–3.45(1H, m), 3.66–3.70(2H, m), 4.34–4.40(1H, m), 4.49–4.55(1H, m),5.19(1H, d, J = 8.1 Hz), 6.66(1H, br-s), 7.24(2H, d, J = 7.8 Hz),7.66(2H, d, J = 7.8 Hz).

Examples of Formulations and Tests

The examples of the formulations and the activity tests of thefungicides according to the invention will be shown below. In thefollowing examples, the term “part” hereinafter used means “part byweight” or “% by weight”.

Example of Formulation 1 Granules

Thirty parts of the compound of the invention (30), 22 parts ofbentonite, 45 parts of talc, 3 parts of Sorpol 5060 (surfactant: TohoChemical Industry Co., Ltd., brand name) and a small quantity ofantifoamer were kneaded uniformly, granulated with a basket granulatingmachine, and dried to obtain 100 parts of granules.

Example of Formulation 2 Granules

Fifteen parts of the compound of the invention (241), 60 parts ofbentonite, 21 parts of talc, 1 part of sodium dodecylbenzenesulfonate, 1part of polyoxyethylenealkyl allyl ether and 2 parts of sodiumligninsulfonate were mixed, kneaded uniformly with the addition of asuitable quantity of water, granulated with a basket granulatingmachine, and dried to obtain 100 parts of granules.

Example of Formulation 3: Wettable Powder

Fifty parts of the compound of the invention (290), 40 parts of calciumcarbonate, 5 parts of Sorpol 5039 (a mixture of anionic surfactant andwhite carbon: Toho Chemical Industry Co., Ltd., brand name) and 5 partsof white carbon were mixed and milled uniformly to obtain a wettablepowder.

Example of Formulation 4 Wettable Powder

Thirty parts of the compound of the invention (526), 63 parts ofkaolinite, 5 parts of Sorpol 5039 (a mixture of anionic surfactant andwhite carbon: Toho Chemical Industry Co., Ltd., brand name) and 2 partsof white carbon were mixed and milled uniformly to obtain wettablepowder.

Example of Formulation 5 Emulsion

Twenty parts of the compound of the invention (674), 55 parts of xylene,20 parts of N,N-dimethylformamide and 5 parts of Sorpol 2680(surfactant) were mixed uniformly to obtain an emulsion concentrate.

Example of Formulation 6 Flowable

Of all the ingredients of 40 parts of the compound of the invention(742), 5 parts of Sorpol 3353 (a nonionic surfactant: Toho ChemicalIndustry Co., Ltd., brand name), 5 parts of 1% aqueous solution ofxanthan gum, 40 parts of water and 10 parts of ethylene glycol, thoseexcept the active ingredient were dissolved uniformly, and then thecompound of the invention was added. After fully stirred, the mixturewas wet milled with a sand mill to obtain a flowable.

Example of Formulation 7 Powder

Five parts of the compound of the invention (807) and 95 parts of claywere admixed to obtain powder.

Test Example 1: Test of Rice Blast Controlling Effect (Spray ApplicationTest)

A diluted solution of a wettable powder prepared at 500 ppm inaccordance with formulation Example 4 was applied to a rice pot(variety: Koshihikari; 2-leaf stage) and air-dried. The plant was putinto an artificial weather room (set conditions: 22° C., 12-hour darklight cycle) and spray-inoculated with a suspension of Pyriculariaoryzae spores. The artificial weather room was kept at high humidity,and the plant was examined after 7 days. The preventive value wascalculated by the following equation and the controlling effect wasevaluated based on the criteria shown in the following table. Theresults are shown in Table 3.

Preventive value (%)=(1−the number of lesions in treated plot/the numberof lesions in untreated plot)×100

Effect Preventive value A 100% B 80% or more and less than 100% C 50% ormore and less than 80% D less than 50%

As a control, the following chemicals were used.

TABLE 3 Rice blast controlling effect test (Spray Application Test)Comp. No. Grade of Effect 4 A 26 A 30 A 66 A 215 A 216 A 236 A 237 A 238A 239 A 240 A 241 A 242 A 243 A 245 A 246 A 247 A 279 A 284 A 289 A 290A 384 A 387 A 464 B 469 B 470 A 471 A 504 B 526 A 530 A 596 A 600 A 636A 674 A 677 A 739 A 742 A 804 A 807 A 1049 A 1050 A 1063 A 1066 A 1078 A1081 A 1123 A 1126 A 1138 A 1141 A 1153 A 1156 A 1168 A 1171 A 1183 A1186 A 1198 A 1201 A 1213 A 1216 A 1228 A 1231 A 1258 A 1261 A 1273 A1276 A Formula (7) D Formula (8) D

Test Example 2: Test of Rice Blast Controlling Effect (Water SurfaceApplication)

Rice seedlings (variety: Koshihikari; 3-leaf stage) were planted in1/5000 are Wagner pots and grown for one week in a green house. Granulesprepared in accordance with Formulation Example 2 were applied to watersurface in each pot at a rate of 3 kg/10 ares. After 30 days from theapplication, a liquid suspension of Pyricularia oryzae spores wasdirectly sprayed to the rice plants. The rice plants were placed underthe conditions of 25° C. and high humidity for 1 week, and the number oflesions was checked. The preventive value was calculated by thefollowing equation and the controlling effect was evaluated based on thefollowing standard. The results are shown in Table 4. As a control, thesame chemical as in Test Example 1 was used.

Preventive value (%)=(1−the number of lesions in treated plot/the numberof lesions in untreated plot)×100

Effect Preventive value A From 80% to 100% B 50% or more and less than80% C less than 50%

TABLE 4 Rice blast controlling effect test (Water surface application)Comp. No. Grade of Effect 4 A 26 A 30 A 66 A 215 A 216 A 236 A 237 A 238A 239 A 240 A 241 A 242 A 243 A 245 A 246 A 247 A 279 A 284 A 289 A 290A 384 A 387 A 464 B 469 B 470 A 471 A 504 B 526 A 530 A 596 A 600 A 636A 674 A 677 A 739 A 742 A 804 A 807 A 1049 A 1050 A 1063 A 1066 A 1078 A1081 A 1123 A 1126 A 1138 A 1141 A 1153 A 1156 A 1168 A 1171 A 1183 A1186 A 1198 A 1201 A 1213 A 1216 A 1228 A 1231 A 1258 A 1261 A 1273 A1276 A Formula (7) C Formula (8) C

Test Example 3: Test of Rice Blast Controlling Effect (Nursery BoxTreatment)

Rice seedlings (variety: Koshihikari; 2-leaf stage) raised in a nurserybox for rice (30 cm×60 cm×3 cm) were treated with granules prepared inaccordance with Formulation Example 1 in a quantity of 50 g per box.After 3 days, the rice seedlings were transplanted into a 1/5000 areWagner in area and raised in a greenhouse. Thirty days after thetransplantation, the plant was spray-inoculated with a suspension ofPyricularia oryzae spores, allowed to keep under the conditions of 25°C. and high humidity for 1 week, and the number of lesions was counted.The preventive value was calculated by the following equation and thecontrolling effect was evaluated based on the same criteria as in TestExample 2. The results are shown in Table 5. As a control, the samechemical as in Test Example 1 was used.

Preventive value (%)=(1−the number of lesions in treated plot/the numberof lesions in untreated plot)×100

TABLE 5 Test of rice blast controlling effect (Nursery box treatment)Comp. No. Grade of Effect 4 A 26 A 30 A 66 A 215 A 216 A 236 A 237 A 238A 239 A 240 A 241 A 242 A 243 A 245 A 246 A 247 A 279 A 284 A 289 A 290A 384 A 387 A 464 B 469 B 470 A 471 A 504 B 526 A 530 A 596 A 600 A 636A 674 A 677 A 739 A 742 A 804 A 807 A 1049 A 1050 A 1063 A 1066 A 1078 A1081 A 1123 A 1126 A 1138 A 1141 A 1153 A 1156 A 1168 A 1171 A 1183 A1186 A 1198 A 1201 A 1213 A 1216 A 1228 A 1231 A 1258 A 1261 A 1273 A1276 A Formula (7) C Formula (8) C

INDUSTRIAL APPLICABILITY

The diamine derivative according to this invention exhibit an excellentrice blast controlling effect, but, on the other hand, does not injureuseful crops; therefore, it is very useful as an agricultural andhorticultural fungicide.

1. A diamine derivative, represented by the following general formula(1):

wherein R1 represents an alkyl group with 1 to 6 carbon atoms providedthat the alkyl group is not a tert-butyl, a cycloalkyl group with 3 to 6carbon atoms, an alkenyl group with 2 to 6 carbon atoms, a cycloalkenylgroup with 3 to 6 carbon atoms, an alkynyl group with 2 to 6 carbonatoms, an arylalkyl group which may be substituted, a heteroarylalkylgroup which may be substituted, an aryl group which may be substituted,or a heteroaryl group which may be substituted; R2 and R7 independentlyrepresent a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, acycloalkyl group with 3 to 6 carbon atoms, an alkenyl group with 2 to 6carbon atoms, a cycloalkenyl group with 3 to 6 carbon atoms, an alkynylgroup with 2 to 6 carbon atoms, an arylalkyl group which may besubstituted, an aryl group which may be substituted, or an acyl group;R3 and R4 independently represent a hydrogen atom, an alkyl group with 1to 6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms, analkenyl group with 2 to 6 carbon atoms, a cycloalkenyl group with 3 to 6carbon atoms, an alkynyl group with 2 to 6 carbon atoms, an arylalkylgroup which may be substituted, a heteroarylalkyl group which may besubstituted, an aryl group which may be substituted or a heteroarylgroup which may be substituted, or a cycloalkyl group with 3 to 6 carbonatoms including an attached carbon atom; R5 and R6 independentlyrepresent a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, acycloalkyl group with 3 to 6 carbon atoms, an alkenyl group with 2 to 6carbon atoms, a cycloalkenyl group with 3 to 6 carbon atoms, an alkynylgroup with 2 to 6 carbon atoms, an arylalkyl group which may besubstituted, or an aryl group which may be substituted; provided thatthe case is excluded where R3, R4, R5 and R6 all represent a hydrogenatom or where any one of R3, R4, R5 and R6 represents a methyl groupwhich may be substituted and the others represent a hydrogen atom, andR8 represents an aryl group which may be substituted or a heteroarylgroup which may be substituted.
 2. The diamine derivative according toclaim 1, wherein R1 represents an alkyl group with 1 to 6 carbon atomsprovided that the alkyl group is not a tert-butyl, a cycloalkyl groupwith 3 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, anarylalkyl group which may be substituted, a heteroarylalkyl group whichmay be substituted, an aryl group which may be substituted, or aheteroaryl group which may be substituted; R2 and R7 independentlyrepresent a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, acycloalkyl group with 3 to 6 carbon atoms, an arylalkyl group which maybe substituted, an aryl group which may be substituted, or an acylgroup; R3 and R4 independently represent a hydrogen atom, an alkyl groupwith 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms,an alkenyl group with 2 to 6 carbon atoms, an arylalkyl group which maybe substituted, a heteroarylalkyl group which may be substituted, anaryl group which may be substituted or a heteroaryl group which may besubstituted, or a cycloalkyl group with 3 to 6 carbon atoms including anattached carbon atom; and R5 and R6 independently represent a hydrogenatom, an alkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3to 6 carbon atoms, an arylalkyl group which may be substituted, or anaryl group which may be substituted; provided that the case is excludedwhere R3, R4, R5 and R6 all represent a hydrogen atom or where any oneof R3, R4, R5 and R6 represents a methyl group which may be substitutedand the others represent a hydrogen atom.
 3. The diamine derivativeaccording to claim 2, wherein R2 and R7 independently represent ahydrogen atom, an alkyl group with 1 to 6 carbon atoms, or an acylgroup; R3 and R4 independently represent a hydrogen atom, an alkyl groupwith 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms,an arylalkyl group which may be substituted, an aryl group which may besubstituted, or a cycloalkyl group with 3 to 6 carbon atoms including anattached carbon atom; and R5 and R6 independently represent a hydrogenatom, an alkyl group with 1 to 6 carbon atoms, an arylalkyl group whichmay be substituted, or an aryl group which may be substituted; providedthat the case is excluded where R3, R4, R5 and R6 all represent ahydrogen atom or where any one of R3, R4, R5 and R6 represents a methylgroup which may be substituted and the others represent a hydrogen atom.4. The diamine derivative according to claim 3, wherein R2 and R7represent a hydrogen atom.
 5. A diamine derivative, represented by thefollowing general formula (9):

wherein R9 represents an alkyl group with 1 to 6 carbon atoms, acycloalkyl group with 3 to 6 carbon atoms, an alkenyl group with 2 to 6carbon atoms, a cycloalkenyl group with 3 to 6 carbon atoms, an alkynylgroup with 2 to 6 carbon atoms, an arylalkyl group which may besubstituted, a heteroarylalkyl group which may be substituted, a phenylgroup, a phenyl group which is substituted at the fourth position, or aheteroaryl group which may be substituted; R10 and R15 independentlyrepresent a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, acycloalkyl group with 3 to 6 carbon atoms, an alkenyl group with 2 to 6carbon atoms, a cycloalkenyl group with 3 to 6 carbon atoms, an alkynylgroup with 2 to 6 carbon atoms, an arylalkyl group which may besubstituted, an aryl group which may be substituted, or an acyl group;one of R11 and R12 represents a methyl group, and the other represents ahydrogen atom; R13 and R14 represent a hydrogen atom, respectively; andR16 represents a phenyl group, a phenyl group which is substituted atthe fourth position, or a heteroaryl group which may be substituted. 6.The diamine derivative according to claim 5, wherein R9 represents analkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an arylalkylgroup which may be substituted, a heteroarylalkyl group which may besubstituted, a phenyl group, a phenyl group which is substituted at thefourth position, or a heteroaryl group which may be substituted; and R10and R15 represent a hydrogen atom, an alkyl group with ito 6 carbonatoms, a cycloalkyl group with 3 to 6 carbon atoms, an arylalkyl groupwhich may be substituted, an aryl group which may be substituted, or anacyl group, independently.
 7. The diamine derivative according to claim6, wherein R10 and R15 independently represent a hydrogen atom, an alkylgroup with 1 to 6 carbon atoms, or an acyl group.
 8. The diaminederivative according to claim 7, wherein at R10 and R15 represent ahydrogen atom, respectively.
 9. A fungicide, wherein it contains thediamine derivative according to claim 8 as an active ingredient.
 10. Aprocess for producing the diamine derivative according to claim 1,wherein a compound having the following general formula (2):

wherein R1, R2, R3, R4, R5, R6 and R7 represent the same groups as thoseof the compounds according to claim 1, is reacted with a compound havingthe following general formula (3):

wherein R8 represents the same group as that of the compound accordingto claim 1, and X represents a leaving group.
 11. A process forproducing the diamine derivative according to claim 1, wherein acompound of the general formula (2) is condensed with a compound havingthe following general formula (4):

wherein R8 represents the same group as that of the compounds accordingto claim
 1. 12. A process for producing the diamine derivative accordingto claim 1, wherein a compound having the following general formula (5):

wherein R2, R3, R4, R5, R6, R7 and R8 represent the same groups as thoseof the compound according to claim 1, is reacted with a compound havingthe following general formula (6):

wherein R1 represents the same group as that of the compound accordingto claim 1, and X represents a leaving group.
 13. A process forproducing the diamine derivative according to claim 5, wherein acompound having the following general formula (10):

wherein R9, R10, R11, R12, R13, R14 and R15 represent the same groups asthose of the compounds according to claim 5, is reacted with a compoundhaving the following general formula (11):

wherein R16 represents the same group as that of the compound accordingto claim 5, and X represents a leaving group.
 14. A process forproducing the diamine derivative according to claim 5, wherein acompound of the general formula (10) is condensed with a compound havingthe following general formula (12):

wherein R16 represents the same group as that of the compounds accordingto claim
 5. 15. A process for producing the diamine derivative accordingto claim 5, wherein a compound having the following general formula(13):

wherein R10, R11, R12, R13, R14, R15 and R16 represent the same groupsas those of the compound according to claim 5, is reacted with acompound having the following general formula (14):

wherein R9 represents the same group as that of the compound accordingto claim 5, and X represents a leaving group.
 16. A fungicide, whereinit contains the diamine derivative according to claim 1 as an activeingredient.
 17. A fungicide, wherein it contains the diamine derivativeaccording to claim 5 as an active ingredient.